Water → HCID 66653182, compound

HRID 1524272Notes

Reaction equation

HRID 1524272 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[C:18](=[O:28])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=2)[CH:8]=1)C.O>CO.O1CCCC1>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([NH:19][C:18]([C@H:14]2[CH2:15][CH2:16][CH2:17][N:13]2[C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:6]([OH:29])=[O:5])=[O:28])=[CH:25][CH:24]=1)#[N:27]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66653188HCID 66653188, compound

Product 1

HCID 66653182HCID 66653182, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Add lithium hydroxide (0.03 g, 1.3 mmol) to the crude 3-[(R)-2-(4-cyano-phenylcarbamoyl)-pyrrolidin-1-yl]-benzoic acid ethyl ester (0.05 g, 0.14 mmol) in a 1:1:1 mixture of water:MeOH/tetrahydrofuran (3 mL). Stir the mixture at room temperature for 15 h then wash with EtOAc. Adjust the pH of the aqueous phase to slightly acidic by the addition of a 2 N solution of hydrochloric acid. Extract the mixture with methylene chloride, dry the combined organic phase over anhydrous sodium sulfate and concentrate under a stream of nitrogen to provide 0.020 g of 3-[(R)-2-(4-cyano-phenylcarbamoyl)-pyrrolidin-1-yl]-benzoic acid as a yellow oil.

Workup

  1. washthen wash with EtOAc
  2. additionslightly acidic by the addition of a 2 N solution of hydrochloric acid
  3. extractionExtract the mixture with methylene chloride
  4. dry with materialdry the combined organic phase over anhydrous sodium sulfate
  5. concentrationconcentrate under a stream of nitrogen

Sources & evidence

ORD record
ord-695e6befca9b4fa3b7ed36b3f8f342da
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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