Methanol → HCID 11646163, compound

HRID 554487Notes

Reaction equation

HRID 554487 reaction equation
CO.C([O:10][C@@H:11]1[C@@H:16]([O:17]CC2C=CC=CC=2)[C@H:15]([O:25]CC2C=CC=CC=2)[C@@H:14]([CH2:33][O:34]CC2C=CC=CC=2)[CH2:13][C:12]1(OC(=O)C)[C:42]1[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[CH:43]=1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].[C].C1COCC1>[OH:34][CH2:33][C@H:14]1[CH2:13][C@@H:12]([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][C:49]3[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=3)[CH:43]=2)[C@H:11]([OH:10])[C@@H:16]([OH:17])[C@@H:15]1[OH:25]

Participants

5

Reactant 2

HCID 887MethanolHCID 67461057HCID 67461057, compound

Product 1

HCID 11646163HCID 11646163, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a methanol (0.2 mL)-THF (0.2 mL) solution of acetic acid [2R,3S,4R,5R]-2,3,4-trisbenzyloxy-5-benzyloxymethyl-1-[3-(4-methoxybenzyl)phenyl]cyclohexyl ester (4.2 mg), a 20% palladium hydroxide-carbon (3 mg) was added and the mixture solution was stirred under a hydrogen atmosphere for three hours. The reaction mixture was filtered and the filtrate was concentrated and the obtained residue was purified by preparative TLC [developing solution=dichloromethane:methanol (9:1)] to obtain the title compound (1.7 mg) as a single diastereomer.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe obtained residue was purified by preparative TLC [developing solution=dichloromethane:methanol (9:1)]

Sources & evidence

ORD record
ord-f33f28d0d6a44bbe998f6e7676aa0e84
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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