Sodium Hydroxide → HCID 66972752, compound

HRID 1367829Notes

Reaction equation

HRID 1367829 reaction equation
C[O:2][C:3](=[O:27])[C@@H:4]([NH:14][CH:15]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:16]([F:19])([F:18])[F:17])[CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[OH-].[Na+]>CO>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[S:7][CH2:6][CH2:5][C@H:4]([NH:14][CH:15]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:16]([F:19])([F:17])[F:18])[C:3]([OH:27])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66972332HCID 66972332, compound

Product 1

HCID 66972752HCID 66972752, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(Pyridin-2-ylsulfanyl)-2(S)-[2,2,2-trifluoro-1-(4-fluorophenyl)ethylamino]butyric acid methyl ester was dissolved in methanol (2 mL) and 1N NaOH (1.2 mL) was added. After stirring for 2 h, methanol was removed and the aqueous layer was acidified to pH 5. After extracting with ethyl acetate the organic layer was dried and concentrated to give 4-(pyridin-2-ylsulfanyl)-2(S)-[2,2,2-trifluoro-1-(4-fluorophenyl)ethylamino]butyric acid as an oil which was then converted to the title compound as described above. MS (485.5 M+1)

Workup

  1. custommethanol was removed
  2. extractionAfter extracting with ethyl acetate the organic layer
  3. customwas dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e71195013844a228227c8610db84af2
Source dataset
uspto-grants-2011_02
Patent number
US07893093B2

Reaction notes

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