Lithium Hydroxide → 2-{[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid

HRID 29746Notes

Reaction equation

HRID 29746 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:48])[CH:6]([O:18][P:19]([CH:22]([NH:26][C:27](=[O:47])[CH:28]([NH:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:23]([CH3:25])[CH3:24])([OH:21])=[O:20])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(OCC)(=O)C>C(#N)C>[CH2:40]([O:39][C:37]([NH:36][CH:28]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:27]([NH:26][CH:22]([P:19]([OH:21])([O:18][CH:6]([CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[C:5]([OH:48])=[O:4])=[O:20])[CH:23]([CH3:25])[CH3:24])=[O:47])=[O:38])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 570512352-{[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid methyl ester

Product 1

HCID 571114642-{[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1 M LiOH (3.5 mL) was added to a solution of 2-{[1-(2-benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid methyl ester (211 mg, 0.32 mmol) in acetonitrile (3.5 mL) and the mixture was stirred for 3 h. Ethyl acetate was added and the mixture was washed with 1 M HCl, dried and concentrated to give crude 2-{[1-(2-benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid (208 mg, 100%).

Workup

  1. washthe mixture was washed with 1 M HCl
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f66b2b6bb5b649178e2771510826a08e
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Reaction notes

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