Dimethylformamide → 2(R)-[(4-methoxycarbonylbenzyl)-(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester

HRID 1006093Notes

Reaction equation

HRID 1006093 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[C@H:10]([NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH:11]([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([CH2:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1)(O)=O.[C:39](=O)([O-])[O-:40].[K+].[K+].CN(C)C=[O:48]>>[CH2:1]([O:8][C:9](=[O:26])[C@H:10]([N:14]([CH2:35][C:34]1[CH:33]=[CH:32][C:31]([C:30]([O:40][CH3:39])=[O:48])=[CH:38][CH:37]=1)[S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)(=[O:17])=[O:16])[CH:11]([CH3:13])[CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 45190564-(Bromomethyl)phenylacetic acidHCID 15429254N-(4-methoxybenzenesulfonyl)-D-valine benzyl ester

Product 1

HCID 697630592(R)-[(4-methoxycarbonylbenzyl)-(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester

Procedure

To a solution of 2(R)-(4-methoxybenzenesulfonylamino)-3-methylbutyric acid benzyl ester (1 g, 2.65 mmol) and 4-carboxymethylbenzyl bromide (0.577 g, 2.52 mmol) in dry dimethylformamide (60 mL) was added potassium carbonate (0.55 g, 4 mmol). The reaction mixture was stirred overnight and then condensed on the rotoevaporator. Purification by flash chromatography on a silica gel column using (5%) ethyl acetate/hexanes as the eluant gave 2(R)-[(4-methoxycarbonylbenzyl)-(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester (0.965 g) which was converted to N-hydroxy-2(R)-[(4-methoxycarbonylbenzyl)-(4-methoxybenzene-sulfonyl)amino]-3-methylbutyramide by following Steps 6 and 7 in Example 1, above.

Workup

  1. customcondensed on the rotoevaporator
  2. customPurification by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-b3d1cf7be8ac43a399023af6422f022a
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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