m-Chloroperbenzoic acid → tert-Butyl 5-(4-(4-bromo-2-ethylphenyl)butanamido)-2-(isopropylsulfonyl)benzyl(methyl)carbamate

HRID 735545Notes

Reaction equation

HRID 735545 reaction equation
C1([O:7][C:8](=O)[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH:19]([CH3:21])[CH3:20])(=[O:18])=[O:17])=[C:12]([CH2:22][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:24])[CH:11]=2)C=CC=CC=1.[Br:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42]C(NC2C=CC(SC(C)C)=C(C=2)CN(C)C(=O)OC(C)(C)C)=O)=[C:36]([CH2:66][CH3:67])[CH:35]=1.C1C=C(Cl)C=C(C(OO)=O)C=1>>[Br:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42][C:8]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH:19]([CH3:21])[CH3:20])(=[O:17])=[O:18])=[C:12]([CH:11]=2)[CH2:22][N:23]([CH3:24])[C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:7])=[C:36]([CH2:66][CH3:67])[CH:35]=1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 57842757tert-Butyl 5-(4-(4-bromo-2-ethylphenyl)butanamido)-2-(isopropylthio)benzyl(methyl)carbamateHCID 57842905[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid phenyl ester

Product 1

HCID 57842767tert-Butyl 5-(4-(4-bromo-2-ethylphenyl)butanamido)-2-(isopropylsulfonyl)benzyl(methyl)carbamateYield 69%

Procedure

Using a procedure analogous to that described for the preparation of 16G, 21B (0.700 g, 1.25 mmol) was reacted with mCPBA (0.695 g, 3.10 mmol) to give 21C (0.513 g, 69%). MS (ESI) m/z 595, 597.4 (M+H)+.

Sources & evidence

ORD record
ord-0b90747e3d69470d87caec24d2d59e1c
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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