Water → (2S)-2-(1-Benzothiophen-2-ylformamido)-4-methylpentanoic acid

HRID 413233Notes

Reaction equation

HRID 413233 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:23])[C@H:6]([CH2:19][CH:20]([CH3:22])[CH3:21])[NH:7][C:8]([C:10]1[S:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[CH:11]=1)=[O:9].O.[CH]Cl>C1COCC1.O>[S:14]1[C:10]([C:8]([NH:7][C@H:6]([C:5]([OH:23])=[O:4])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:9])=[CH:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 6432229CID 6432229HCID 32044690n-Benzo[b]thiophene-2-ylcarbonyl-l-leucine methyl ester

Product 1

HCID 25324072(2S)-2-(1-Benzothiophen-2-ylformamido)-4-methylpentanoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (1.41 g, 59 mmol) was added in one portion to a stirred solution of N-benzo[b]thiophene-2-ylcarbonyl-L-leucine methyl ester (8.99 g, 29.4 mmol) in THF/H2O (1/1, 300 ml). After stirring for 12 hours at room temperature, the mixture was poured into water and acidifed to pH 1 with cHCl and extracted with Et2O (×2). Evaporation under reduced pressure afforded the title compound as a yellow solid, 6.1 g, 71% yield.

Workup

  1. extractionextracted with Et2O (×2)
  2. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-bdf69c87319240f082218c49d0935720
Source dataset
uspto-grants-2003_05
Patent number
US06566373B2

Reaction notes

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