Lithium Hydroxide → (S)-4,4-Difluoro-2-[(perhydro-1,4-oxazepine-4-carbonyl)-amino]-pentanoic acid

HRID 1455591Notes

Reaction equation

HRID 1455591 reaction equation
C[O:2][C:3](=[O:20])[C@@H:4]([NH:10][C:11]([N:13]1[CH2:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12])[CH2:5][C:6]([F:9])([F:8])[CH3:7].[OH-].[Li+]>O1CCCC1.CO.O>[F:9][C:6]([F:8])([CH3:7])[CH2:5][C@H:4]([NH:10][C:11]([N:13]1[CH2:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12])[C:3]([OH:20])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57535348(S)-4,4-Difluoro-2-[(perhydro-1,4-oxazepine-4-carbonyl)-amino]-pentanoic acid methyl ester

Product 1

HCID 57535332(S)-4,4-Difluoro-2-[(perhydro-1,4-oxazepine-4-carbonyl)-amino]-pentanoic acidYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(S)-4,4-Difluoro-2-[(perhydro-1,4-oxazepine-4-carbonyl)-amino]-pentanoic acid methyl ester (0.38 g, 1.29 mmol) is dissolved in tetrahydrofuran/methanol (15 mL/10 mL) and lithium hydroxide (35 mg, 1.40 mmol) dissolved in water (5 mL) added. The reaction is stirred at RT for 18 h, and then the methanol/tetrahydrofuran is removed in vacuo. The residue is acidified with 6M hydrochloric acid (0.25 mL) and extracted with dichloromethane (3×20 mL), dried (Na2SO4), and concentrated to yield (S)-4,4-Difluoro-2-[(perhydro-1,4-oxazepine-4-carbonyl)-amino]-pentanoic acid as a solid (0.36 g, 99%).

Workup

  1. additionadded
  2. customthe methanol/tetrahydrofuran is removed in vacuo
  3. extractionextracted with dichloromethane (3×20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2f8b849f352040b995527093362eb8d8
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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