tert-Butanol → Tert-Butyl [({2-[4-(1,1-dioxido-4-oxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl)-3-benzyloxyphenyl]ethyl}amino)sulfonyl]carbamate

HRID 660683Notes

Reaction equation

OC(C(F)(F)F)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19](=[O:30])[CH2:18]2)=[C:13]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:12]=1.Cl[S:40]([N:43]=[C:44]=[O:45])(=[O:42])=[O:41].[C:46]([OH:50])([CH3:49])([CH3:48])[CH3:47]>>[O:22]=[S:21]1(=[O:23])[N:20]([CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[C:19](=[O:30])[CH2:18][N:17]1[C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][NH:8][S:40]([NH:43][C:44](=[O:45])[O:50][C:46]([CH3:49])([CH3:48])[CH3:47])(=[O:42])=[O:41])=[CH:12][C:13]=1[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Reactant 3

HCID 6386tert-Butanol

HCID 70918Chlorosulfonyl isocyanate

HCID 866325725-[4-(2-Aminoethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA Salt

Product 1

HCID 86632582Tert-Butyl [({2-[4-(1,1-dioxido-4-oxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl)-3-benzyloxyphenyl]ethyl}amino)sulfonyl]carbamate

Procedure

The title compound is prepared from 5-[4-(2-aminoethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA salt (Example 67, step A), chlorosulfonyl isocyanate and t-butanol analogous to Example 55, step D.

Sources & evidence

ORD record: ord-33e5dd6bc5634f58a35281f87e1fb85d
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Reaction notes

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