Lithium hydroxide, monohydrate → 4-amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine

HRID 393436Notes

Reaction equation

HRID 393436 reaction equation
C[O:2][C:3](=[O:30])[C@H:4]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)[NH:5][C:6]([C:8]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].O.[OH-].[Li+]>C1COCC1.O>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C@@H:4]([C:3]([OH:30])=[O:2])[NH:5][C:6]([C:8]2([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 544852054-Amino-N-[[1[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester

Product 1

HCID 540857504-amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanineYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester (280 mg, 0.68 mmol) in THF (12 mL) was treated with a solution of lithium hydroxide hydrate (100 mg, 2.4 mmol) in water (2 mL) and the mixture was stirred for 3 hr. The mixture was concentrated and the residue was acidified with 6 H HCl to give a white sticky solid. Trituration with water and drying under high vacuum afforded crude 4-amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine (200 mg) suitable for use in the next step.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a white sticky solid
  3. dry with materialTrituration with water and drying under high vacuum

Sources & evidence

ORD record
ord-57e705f58b2a42dbb9073aaea2b78c61
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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