Hydrochloric Acid → HCID 68605830, compound

HRID 1593306Notes

Reaction equation

HRID 1593306 reaction equation
[OH:1][C@@H:2]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:3]([NH:5][C@@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([O:9]C)=[O:8])=[O:4].[OH-].[Li+].Cl>C1COCC1.O>[OH:1][C@@H:2]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:3]([NH:5][C@@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10636385HCID 10636385, compound

Product 1

HCID 68605830HCID 68605830, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2S)-{[(2S)-2-hydroxy-4-methylpentanoyl]amino}(phenyl)acetate (76a) (4.185 g) in THF (30 ml) and water (15 ml) cooled to 0° C. was added lithium hydroxide (1.45 g) portion wise. The mixture was stirred at RT overnight. The reaction was acidified with 1N hydrochloric acid until pH=1. The mixture was concentrated to remove THF and extracted with Ethyl acetate (3×). The organic layers were washed with water, brine, dried, filtered and evaporated to afford the title compound as a tacky white solid. Trituration with dichloromethane/diethyl ether yielded a free flowing solid (3.85 g). 1H NMR (300 MHz, CDCl3) δ 0.89-0.94 (m, 6H), 1.45-1.63 (m, 2H), 1.76-1.83 (m, 1H), 3.25 (bs, 2H), 4.20-4.25 (m, 1H), 5.56 (d, 1H, J=7 Hz), 7.35-7.39 (m, 5H), 7.53 (d, 1H, J=7 Hz). MS APCI, m/z=266 (M+1). LC/MS: 1.68 min.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove THF
  3. extractionextracted with Ethyl acetate (3×)
  4. washThe organic layers were washed with water, brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e621301b40d14b8da633e9a8cbf2a4f7
Source dataset
uspto-grants-2007_11
Patent number
US07294622B2

Reaction notes

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