(S)-4,4-difluoro-2-[(morpholine-4-carbonyl)-amino]-5-phenyl-pentanoic acid methyl ester → (S)-4,4-Difluoro-2-[(morpholine-4-carbonyl)-amino]-5-phenyl-pentanoic acid

HRID 1455569Notes

Reaction equation

HRID 1455569 reaction equation
C[O:2][C:3](=[O:25])[C@@H:4]([NH:16][C:17]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18])[CH2:5][C:6]([F:15])([F:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO.O.O>[F:15][C:6]([F:14])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][C@H:4]([NH:16][C:17]([N:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1)=[O:18])[C:3]([OH:25])=[O:2]

Participants

4

Reactant 1

HCID 57535362(S)-4,4-difluoro-2-[(morpholine-4-carbonyl)-amino]-5-phenyl-pentanoic acid methyl ester

Product 1

HCID 57535341(S)-4,4-Difluoro-2-[(morpholine-4-carbonyl)-amino]-5-phenyl-pentanoic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (S)-4,4-difluoro-2-[(morpholine-4-carbonyl)-amino]-5-phenyl-pentanoic acid methyl ester (2.81 g, 7.88 mmol) in MeOH:H2O (2:1 vol, 40 mL) is added LiOH mono hydrate (662 mg, 15.76 mmol). The mixture is stirred at room temperature for 2.5 h, and then diluted with water (30 mL). Methanol is removed in vacuum. The pH is adjusted to pH 1 with 6N HCl and the aqueous layer is extracted with dichloromethane (2×30 mL). The organic layers are dried over magnesium sulfate and concentrated in vacuum to afford (S)-4,4-Difluoro-2-[(morpholine-4-carbonyl)-amino]-5-phenyl-pentanoic acid (2.509 g, 93%).

Workup

  1. customMethanol is removed in vacuum
  2. extractionthe aqueous layer is extracted with dichloromethane (2×30 mL)
  3. dry with materialThe organic layers are dried over magnesium sulfate
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-edfd17856e314f768e693b310f83b4da
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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