Water → HCID 69018038, compound

HRID 1865733Notes

Reaction equation

HRID 1865733 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:42])[C@@H:9]([C:33]([CH3:41])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:34])[CH2:10][NH:11][C@H:12]([C:17]([N:19]([CH3:32])[C@@H:20]([CH:29]([CH3:31])[CH3:30])/[CH:21]=[C:22](\[CH3:28])/[C:23]([O:25]CC)=[O:24])=[O:18])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.O.[OH-].[Li+]>CO>[C:1]([O:5][C:6]([N:8]([CH3:42])[C@@H:9]([C:33]([CH3:41])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:34])[CH2:10][NH:11][C@H:12]([C:17]([N:19]([CH3:32])[C@@H:20]([CH:29]([CH3:31])[CH3:30])/[CH:21]=[C:22](\[CH3:28])/[C:23]([OH:25])=[O:24])=[O:18])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69221574HCID 69221574, compound

Product 1

HCID 69018038HCID 69018038, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl (2E,4S)-4-[(N-{(2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-methyl-3-phenylbutyl}-3-methyl-L-valyl)(methyl)amino]-2,5-dimethyl-2-hexenoate (50 mg, 0.085 mmol, Reference Example 20) is dissolved in methanol (1 ml), tetrahydrofuran (1 ml). To this solution is added water (0.5 ml) and solid lithium hydroxide (4.1 mg). The resulting mixture is stirred at room temperature for 15 hours. The organic solvents are removed in vacuo, and the residual aqueous mixture is cooled with an ice water bath, and acidified to pH 5.5-6.0 with aqueous 1N aqueous citric acid solution. The precipitate is collect by filtration, and the solid is washed with a cold water, and dried over high vacuum. Alternatively, the product can be purified by using preparative HPLC. (40 mg, 80%) MS [M+H] 588.2

Workup

  1. customThe organic solvents are removed in vacuo
  2. temperaturethe residual aqueous mixture is cooled with an ice water bath
  3. filtrationThe precipitate is collect by filtration
  4. washthe solid is washed with a cold water
  5. customdried over high vacuum
  6. customAlternatively, the product can be purified

Sources & evidence

ORD record
ord-92588ca0ba6d41af8e95e27adde337ea
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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