Lithium Hydroxide → 4-tert-butoxy-2-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-2-(4-chlorophenyl)-4-oxobutanoic acid

HRID 1427286Notes

Reaction equation

HRID 1427286 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:19]([O:21]C)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>>[C:27]([O:26][C:24](=[O:25])[CH2:23][C:18]([N:13]1[C:14]2[C:10](=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:17]=[CH:16][CH:15]=2)[CH:11]=[CH:12]1)([C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)[C:19]([OH:21])=[O:20])([CH3:29])([CH3:30])[CH3:28]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 705860914-tert-butyl 1-methyl 2-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-2-(4-chlorophenyl)succinate

Product 1

HCID 705646004-tert-butoxy-2-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-2-(4-chlorophenyl)-4-oxobutanoic acid

Procedure

A mixture of the product of step A (1.8 g, 3.4 mmol) and 3 N LiOH (410 mg, 17 mmol) was stirred at room temperature for 3 h. After the solvent was evaporated, the residue was dissolved in ethyl acetate (20 mL), and pH value adjusted to 6-7 with 1 M HCl. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound as colorless oil. LC/MS m/z=515.2[M+H]+.

Workup

  1. customAfter the solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfde2e4b8924470ab7dd95318b5c302a
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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