Methanol → HCID 68415473, compound

HRID 1865318Notes

Reaction equation

[CH2:1]([O:8][CH:9]([C:17](=O)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:30].CO>O1CCCC1>[C:10]([OH:12])(=[O:11])[CH3:9].[NH2:30][CH:17]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

Conditions

Temperature: 90 °C

Procedure

Ru(OAc)2((S)-dm-segphos) (0.138 g, 0.147 mmol), tert-butyl 2-benzyloxy-3-oxo-4-phenylbutanoate (5.00 g, 14.7 mmol), ammonium acetate (1.13 g, 14.7 mmol), methanol (25 mL) and tetrahydrofuran (25 mL) were placed in a 200 mL stainless steel autoclave, and the mixture was stirred at 90° C. under a hydrogen pressure of 3 MPa for 13 hours. After completion of the reaction, the solvent was removed by evaporation to give tert-butyl 3-amino-2-benzyloxy-4-phenylbutanoate acetate as a crude material (6.10 g). The ratio of anti and syn diastereoisomer (86:14) was determined by HPLC analysis using a CHIRALPAK AD-RH column (available from DAICEL CHEMICAL INDUSTRIES, LTD). The enantiomeric excess of the crude product was determined to be 98.6% ee (anti diastereoisomer) and 95.1% ee (syn diastereoisomer) by HPLC analysis using a CHIRALCEL OD-H column after conversion into tert-butyl 3-(4-nitrobenzoylamino)-2-benzyloxy-4-phenylbutanoate.

Workup

customAfter completion of the reaction
customthe solvent was removed by evaporation

Sources & evidence

ORD record: ord-4af0cea68cbb4ae895f72b5367001371
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07626034B2

Reaction notes

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