tert-butyl (4S,5S)-5-((S)-2-((benzyloxy)methyl)-3-methylbutyl)-4-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate → 3-Oxazolidinecarboxylic acid, 5-[(2S)-2-(hydroxymethyl)-3-methylbutyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S,5S)-

HRID 264940Notes

Reaction equation

HRID 264940 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@@H:14]([CH:30]([CH3:32])[CH3:31])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:11]([CH2:33][C@@H:34]([CH:44]([CH3:46])[CH3:45])[CH2:35][O:36]CC2C=CC=CC=2)[O:10][C:9]1([CH3:48])[CH3:47])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@@H:14]([CH:30]([CH3:32])[CH3:31])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:11]([CH2:33][C@@H:34]([CH:44]([CH3:46])[CH3:45])[CH2:35][OH:36])[O:10][C:9]1([CH3:47])[CH3:48])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 23625485tert-butyl (4S,5S)-5-((S)-2-((benzyloxy)methyl)-3-methylbutyl)-4-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 236253313-Oxazolidinecarboxylic acid, 5-[(2S)-2-(hydroxymethyl)-3-methylbutyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S,5S)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3.7 g of 3-tert-butoxycarbonyl-5(S)-(3-benzyloxy-2(S)-isopropyl-propyl)-4(S)-{2(S)-iso-propyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine are hydrogenated in the presence of 1.0 g of 5% Pd/C in 50 ml of tetrahydrofuran for 15 minutes at room temperature and under normal pressure. The reaction mixture is filtered and concentrated by evaporation. The residue is purified by means of FC (140 g of silica gel, ethyl acetate/hexane=1:2). The title compound is obtained: Rf (ethyl acetate/hexane=1:2)=0.28.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated by evaporation
  3. customThe residue is purified by means of FC (140 g of silica gel, ethyl acetate/hexane=1:2)

Sources & evidence

ORD record
ord-0a1fd5eb9f5d4816b87405506c7d35e2
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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