Methanol → HCID 60207251, compound

HRID 493364Notes

Reaction equation

HRID 493364 reaction equation
CO.[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35]CC2C=CC=CC=2)=[C:31]([O:43]CC2C=CC=CC=2)[CH:30]=1)[C:12]([O:14][C@H:15]([CH3:27])[C@H:16]([O:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20])[CH3:17])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCCC1.[Pd]>[OH:43][C:31]1[CH:30]=[C:29]([CH2:28][C@H:11]([NH:10][C:8]([O:7][C:3]([CH3:5])([CH3:4])[CH3:6])=[O:9])[C:12]([O:14][C@H:15]([CH3:27])[C@H:16]([O:18][C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:20])[CH3:17])=[O:13])[CH:34]=[CH:33][C:32]=1[OH:35]

Participants

5

Reactant 2

HCID 887MethanolHCID 60207250HCID 60207250, compound

Product 1

HCID 60207251HCID 60207251, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

200 mg of 10% Pd—C pre-mixed with 10 mL of methanol was added to a solution of (1R,2R)-1-methyl-2-phenylcarbonyloxypropyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate (2.6 g, 3.9 mmol) in 40 mL of tetrahydrofuran under a nitrogen atmosphere. The resulting mixture was stirred under hydrogen at room temperature for 2 hrs. After filtration and washing with methanol, the filtrate was concentrated and chromatography (silica gel, 30% ethyl acetate in hexane) of the residue afforded 1.8 g (95%) of (1R,2R)-1-Methyl-2-phenylcarbonyloxypropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate. MS (ESI) m/z 474.31 (M+H)+ and 472.18 (M−H)−.

Workup

  1. filtrationAfter filtration
  2. washwashing with methanol
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e5a5d782a0634cc486013f1e1583a080
Source dataset
uspto-grants-2009_05
Patent number
US07534813B2

Reaction notes

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