Water → 4-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid

HRID 1823924Notes

Reaction equation

HRID 1823924 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O.[OH-].[Li+]>C1COCC1>[C:11]([O:10][C:8]([NH:7][CH2:6][CH2:5][CH:4]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:3]([OH:23])=[O:2])=[O:9])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 235709514-Tert-butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid methyl ester

Product 1

HCID 221479534-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-tert-butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid methyl ester (12.3 g, 34 mmol) in THF (80 mL)/water (20 mL) was added lithium hydroxide (1.63 g, 68 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated and the residue diluted with water. After extraction with EtOAc, the aqueous phase was acidified to pH 5 by the addition of 2M aqueous hydrochloric acid solution. The aqueous phase was extracted with EtOAc and the extracts dried over magnesium sulfate. Concentration gave the title compound as a pale brown foam (11.54 g, 98%); 1H NMR (400 MHz, DMSO) δ 1.35 (9H, s), 1.74–1.81 (1H, m), 2.03–2.10 (1H, m), 2.81 (2H, m), 3.61 (1H, t), 6.86 (1H, m), 7.28 (1H, dd), 7.54 (1H, dd), 7.59 (1H, d), 12.60 (1H, brs); MS (ES−) m/e=346.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue diluted with water
  3. extractionAfter extraction with EtOAc
  4. additionthe aqueous phase was acidified to pH 5 by the addition of 2M aqueous hydrochloric acid solution
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialthe extracts dried over magnesium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-abcf6e0a239345a1bae17a3dd71407b6
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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