Hydrochloric Acid → HCID 68604940, compound

HRID 1593323Notes

Reaction equation

HRID 1593323 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:17]([O:19]C)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-].[Na+].Cl>CO.[Cl-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][C@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:15])[CH3:16])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68605009HCID 68605009, compound

Product 1

HCID 68604940HCID 68604940, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

A solution of methyl N-[(3,5-difluorophenyl)acetyl]-L-valinate (107a) in methanol (10 mL) was treated with 1N sodium hydroxide solution (2 mL) and stirred for 2 h. At the end of this period the reaction mixture was acidified with 1N hydrochloric acid solution, diluted with saturated sodium chloride and extracted with dichloromethane (100 mL). After drying over anhydrous magnesium sulfate and concentration under reduced pressure the organic layer afforded the title compound (210 mg). 1H NMR (300 MHz, CDCl3)) δ 0.87 (m, 3H), 2.05 (m, 1H), 3.58 (m, 2H), 4.15 (t, 1H, J=8 Hz), 7.07 (m, 3H), 8.30 (m, 1H), 12.61 (s, 1H). MS APCI, m/z=226(M+1) LC/MS: 1.84 min.

Workup

  1. extractionextracted with dichloromethane (100 mL)
  2. dry with materialAfter drying over anhydrous magnesium sulfate and concentration under reduced pressure the organic layer

Sources & evidence

ORD record
ord-986f9befd7ee4a80ba2742e1d5b503bf
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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