2-(4-Bromophenyl)butanoic acid → tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(isopropylthio)benzyl(methyl)carbamate

HRID 735534Notes

Reaction equation

HRID 735534 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([S:30][CH2:31][CH3:32])=[C:18]([CH:29]=2)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:12])=[CH:4][CH:3]=1.[C:33](OC(=O)N(CC1C=C(N)C=CC=1SC(C)C)C)(C)(C)C.BrC1C=CC(C(CC)C(O)=O)=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([S:30][CH:31]([CH3:33])[CH3:32])=[C:18]([CH:29]=2)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:12])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 574722-(4-Bromophenyl)butanoic acidHCID 57842879tert-Butyl-(5-amino-2-(isopropylthio)benzyl)(methyl)carbamateHCID 57956370tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(ethylthio)benzyl(methyl)carbamate

Product 1

HCID 57842807tert-Butyl 5-(4-(4-bromophenyl)butanamido)-2-(isopropylthio)benzyl(methyl)carbamateYield 89%

Procedure

Using a procedure analogous to that used for preparation of 17B, 16E (0.418 g, 1.35 mmol) was reacted with 4-bromophenylbutanoic acid (0.340 g, 1.40 mmol) to give 18A (0.642 g, 89%) as a white solid. MS (ESI) m/z 537.0 (M+H)+.

Sources & evidence

ORD record
ord-b9b7dfa49d1542adac6d6142db2daf41
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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