(4S,5R)-tert-butyl 4-((S)-2-(benzyloxymethyl)-3-methylbutyl)-5-((2,2-dimethylhexanamido)methyl)-2,2-dimethyloxazolidine-3-carboxylate → (4S,5R)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxymethyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 660388Notes

Reaction equation

HRID 660388 reaction equation
C([O:8][CH2:9][C@H:10]([CH:37]([CH3:39])[CH3:38])[CH2:11][C@H:12]1[C@@H:16]([CH2:17][NH:18][C:19](=[O:27])[C:20]([CH3:26])([CH3:25])[CH2:21][CH2:22][CH2:23][CH3:24])[O:15][C:14]([CH3:29])([CH3:28])[N:13]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:26][C:20]([CH3:25])([CH2:21][CH2:22][CH2:23][CH3:24])[C:19]([NH:18][CH2:17][C@H:16]1[O:15][C:14]([CH3:28])([CH3:29])[N:13]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[C@H:12]1[CH2:11][C@H:10]([CH2:9][OH:8])[CH:37]([CH3:38])[CH3:39])=[O:27]

Participants

4

Reactant 1

HCID 68784264(4S,5R)-tert-butyl 4-((S)-2-(benzyloxymethyl)-3-methylbutyl)-5-((2,2-dimethylhexanamido)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 68784232(4S,5R)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxymethyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(4S,5R)-tert-Butyl 4-((S)-2-(benzyloxymethyl)-3-methylbutyl)-5-((2,2-dimethylhexanamido)methyl)-2,2-dimethyloxazolidine-3-carboxylate (3.0 g, 5.5 mol) was dissolved in EtOH (30 mL) and Pd(OH)2/C (300 mg) was added. The reaction mixture was stirred under an atmosphere of hydrogen at rt for about 3-4 h. TLC showed the starting material had been consumed. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give (4S,5R)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxymethyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (2.40 g, 96%) which was used in the next step without purification. 1H NMR (400 MHz, CDCl3): 0.87 (m, 6H), 1.16 (m, 6H), 1.47 (s, 9H), 1.59 (s, 1H), 2.16 (m, 1H), 2.88 (m, 1H), 3.49 (m, 1H), 3.98 (m, 1H); MS: 457 (M++1)

Workup

  1. customhad been consumed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9f8cb2cdf33142c6a31118bd66bd3a34
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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