Sulfamoylating reagents

1. A compound of formula R u N − —S(O) 2 X + , wherein X is a cyclic tertiary amine which is triethylenediamine, diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicycle[4.3.0]non-5-ene, sparteine, N,N′-dimethylpiperazine, or N-ethylmorpholine and R u is an amine protecting group or hydrogen.

2. The compound according to claim 1 , wherein R u is —C(O)OC(R v ) 2 (R w ), wherein:

each R v is independently optionally substituted C 1-10 aliphatic, optionally substituted aryl, or hydrogen;

R w is optionally substituted C 1-10 aliphatic or optionally substituted aryl;

or one R v is optionally substituted C 1-10 aliphatic; and the other R v is taken together with R w to form an optionally substituted C 3-6 cycloaliphatic ring.

3. The compound according to claim 2 , wherein R w is methyl or phenyl.

4. The compound according to claim 2 , wherein each R v independently is methyl, ethyl, butyl, hexyl, octyl, or phenyl.

5. The compound according to claim 2 , wherein R u is —C(O)OC(R v ) 2 (R w ), wherein one R v is optionally substituted C 1-10 aliphatic, and the other R v is taken together with R w to form cyclopropyl, or cyclohexyl.

6. The compound according to claim 1 , wherein R u is —C(O)OCMe 3 , —C(O)OCH 2 Ph, —C(O)N(Ph) 2 , —C(O)OC(Me) 2 Ph, —C(O)OCH(Me)Ph, C(O)OC(Me) 2 Et, —C(O)OC(Et) 2 Ph, —C(O)OC(octyl) 2 Ph,

7. The compound according to claim 6 , wherein R u is —C(O)OCMe 3 .

8. The compound according to claim 1 , wherein R u is —C(O)ON(Ph) 2 .

9. A compound according to claim 1 , wherein X is triethylenediamine.

10. A complex comprising a compound of formula R u N − —S(O) 2 X + and the hydrochloride salt of X, wherein X is a cyclic tertiary amine which is triethylenediamine, diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicycle[4.3.0]non-5-ene, sparteine, N,N′-dimethylpiperazine, or N-ethylmorpholine and R u is an amine protecting group or hydrogen.

11. The complex of claim 10 , wherein the ratio of the compound of formula R u N − —S(O) 2 X + to the hydrochloride salt of X in the complex is less than one.

12. A process for the formation of a compound of formula R u N − —S(O) 2 X + , wherein R u is —C(O)OC(R v ) 2 (R w ), comprising:

I-E) treating (R w )(R v ) 2 C—OH with chlorosulfonylisocyanate;

II-E) treating the reaction mixture formed in step I-E) with X; and

III-E) isolating the sulfamoylating reagent R u N − —S(O) 2 X + formed in step II-E);

wherein

X is a cyclic tertiary amine which is triethylenediamine, diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicycle[4.3.0]non-5-ene, sparteine, N,N′-dimethylpiperazine, or N-ethylmorpholine,

each R v is independently optionally substituted C 1-10 aliphatic, optionally substituted aryl, or hydrogen;

R w is optionally substituted C 1-10 aliphatic or optionally substituted aryl;

or one R v is optionally substituted C 1-10 aliphatic; and the other R v is taken together with R w to form an optionally substituted C 3-6 cycloaliphatic ring.

13. A compound according to claim 9 , wherein R u is —C(O)OCMe 3 .

14. The complex of claim 10 , wherein the ratio of the compound of formula R u N − —S(O) 2 X + to the hydrochloride salt of X in the complex is about one.

15. The complex of claim 10 , wherein the ratio of the compound of formula R u N − —S(O) 2 X + to the hydrochloride salt of X in the complex is more than one.

16. The complex of claim 14 , wherein

X is triethylenediamine and

R u is —C(O)OCMe 3 .

17. The process according to claim 12 , wherein

X is triethylenediamine and

R u is —C(O)OCMe 3 .

18. The compound according to claim 2 , wherein each R v independently is hydrogen, methyl, or ethyl.