Pivaloyl chloride → [(3S)-5-(2,2-Dimethyl-propionyl)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester

HRID 1372969Notes

Reaction equation

HRID 1372969 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>>[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]2[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=2[N:10]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 62493Pivaloyl chlorideHCID 57617767(S)-tert-Butyl (1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)carbamate

Product 1

HCID 69042305[(3S)-5-(2,2-Dimethyl-propionyl)-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester

Procedure

In an analogous manner to that described in Example 103b), the acylation of (S)-(1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester with pivaloyl chloride yielded the title compound as a white solid; MS: m/e=376 (M+H)+.

Sources & evidence

ORD record
ord-52573eb294364658a6926fb8806b8fa4
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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