m-Chloroperbenzoic acid → tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(ethylsulfonyl)benzyl(methyl)carbamate

HRID 735531Notes

Reaction equation

HRID 735531 reaction equation
C1([O:7][C:8](=O)[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16](C(C)C)(=[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(SCC)=C(C=2)CN(C)C(=O)OC(C)(C)C)=O)=[CH:36][CH:35]=1.[CH:65]1C=C(Cl)C=C(C(OO)=O)[CH:66]=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]([CH2:65][CH3:66])(=[O:18])=[O:17])=[C:12]([CH:11]=2)[CH2:22][N:23]([CH3:24])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:7])=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 57842905[3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-(propane-2-sulfonyl)-phenyl]-carbamic acid phenyl esterHCID 57956370tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(ethylthio)benzyl(methyl)carbamate

Product 1

HCID 57842603tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(ethylsulfonyl)benzyl(methyl)carbamateYield 88%

Procedure

Using a procedure analogous to that used for preparation of 16G, 17B (0.460 g, 0.88 mmol) was reacted with mCPBA (0.500 g, 2.23 mmol) to give 17C (0.428 g, 88%) as a white foam. MS (ESI) m/z 555.0 (M+H)+.

Sources & evidence

ORD record
ord-2e1409d974544f1eaa7a107cc12de30e
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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