Lithium Hydroxide → HCID 67496520, compound

HRID 1628309Notes

Reaction equation

HRID 1628309 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:9]([N:11]1[C:19]2[CH:18]=[C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH:16]=[C:15]([C:26]([O:28]C)=[O:27])[C:14]=2[CH2:13][CH2:12]1)=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].C1COCC1>O>[C:1]([O:5][C:6]([C@@H:8]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:9]([N:11]1[C:19]2[CH:18]=[C:17]([C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)[CH:16]=[C:15]([C:26]([OH:28])=[O:27])[C:14]=2[CH2:13][CH2:12]1)=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68759365HCID 68759365, compound

Product 1

HCID 67496520HCID 67496520, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a 20 ml vial were added (S)-methyl 1-(2-(tert-butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylate 54.8.A (900 mg, 1.8 mmole), LiOH)(376 mg, 9.0 mmole), 40 ml of THF, and 10 ml of water. The reaction was stirred at 50° C. for 3 hour at which time the solvent was removed by a stream of nitrogen. The crude product was purified using a silica gel column (eluting with 10% MeOH in DCM) to give (S)-1-(2-(tert-butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylic acid 60.A as a yellow solid (403 mg, 46% yield).

Workup

  1. customwas removed by a stream of nitrogen
  2. customThe crude product was purified
  3. washa silica gel column (eluting with 10% MeOH in DCM)

Sources & evidence

ORD record
ord-99d0fb24c38c4a7e8ccf35781c84778d
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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