Water → Isopropyl (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyrate

HRID 1061652Notes

Reaction equation

HRID 1061652 reaction equation
O.C(=O)([O-])[O-].[Na+].[Na+].[NH2:8][C@@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:10]([OH:17])[C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12].Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>C(OCC)C.C(OCC)(=O)C>[CH2:29]([O:28][C:26]([NH:8][C@@H:9]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:10]([OH:17])[C:11]([O:13][CH:14]([CH3:15])[CH3:16])=[O:12])=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 11736536isopropyl (2RS,3S)-3-amino-2-hydroxy-4-phenylbutyrate

Product 1

HCID 60073836Isopropyl (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyrate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Water (10 ml) and sodium carbonate (763 mg) are added to a solution of isopropyl (2RS,3S)-3-amino-2-hydroxy-4-phenylbutyrate (800 mg, Reference compound No. 4-1) in diethyl ether (10 ml). Benzyl chloroformate (691 mg) is added to the mixture, and the whole is stirred for two hours. Ethyl acetate is added to the reaction mixture, and the whole is washed with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine successively and dried over anhydrous magnesium sulfate. The organic layer is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled reference compound (1.02 g).

Workup

  1. washthe whole is washed with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationThe organic layer is concentrated under reduced pressure
  4. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7698a433d7ff460ba8d5158dc719e85b
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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