1,1-Dimethylethyl N-(aminosulfonyl)carbamate → 1,1-Dimethylethyl N-(aminosulfonyl)carbamate

HRID 1034516Notes

Reaction equation

HRID 1034516 reaction equation
[C:1]([S:4][C@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:7]([CH2:17]O)[CH2:6]1)(=[O:3])[CH3:2].[C:19]([O:23][C:24]([NH:26][S:27]([NH2:30])(=[O:29])=[O:28])=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([NH:26][S:27]([NH2:30])(=[O:29])=[O:28])=[O:25])([CH3:22])([CH3:20])[CH3:21].[C:1]([S:4][C@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C@@H:7]([CH2:17][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[S:27](=[O:28])(=[O:29])[NH2:30])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 107265421,1-Dimethylethyl N-(aminosulfonyl)carbamateHCID 53748200(2R,4R)-Tert-butyl 4-(acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 2

HCID 107265421,1-Dimethylethyl N-(aminosulfonyl)carbamateHCID 54004215(2R,4R)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine

Procedure

N-t-butoxycarbonylsulfamide is prepared in the same manner as in the paragraph (a) of Step A-6 in Preparative Example 7-A. (2R,4R)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol (i.e., a substrate) is allowed to react with the obtained N-t-butoxycarbonylsulfamide in the similar manner as in paragraph (b) of Step A-6 in Preparative Example 7-A under a condition for Step B-6 shown in Table 2 to give (2R,4R)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine. NMR δ(CDCl3) ppm: 1.43(s, 9H), 1.53(s, 9H), 2.34(s, 3H), 2.5(m, 1H), 3.15(dd, J=12.2 Hz, J=6.2 Hz, 1H), 3.58(dd, J=14.8 Hz, J=3.2 Hz, 1H), 3.8 to 4.1(m, 2H), 4.16(dd, J=12.2 Hz, J=7.8 Hz, 1H), 4.4 to 4.7 (m, 1H), 6.11(s, 2H). IR ν (CHCl3) cm-1 : 3360, 3200, 1710, 1688.

Sources & evidence

ORD record
ord-b32fea5b92014906badc37654f32e07e
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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