Hydrochloric Acid → HCID 68604940, compound

HRID 2267662Notes

Reaction equation

HRID 2267662 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-ae17f6c9badc4101afc4a6d6080eb270
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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