ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoate → ethyl (4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-2-octenoate

HRID 1651021Notes

Reaction equation

HRID 1651021 reaction equation
C(OC([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:14]([CH:20]=[C:21]([CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:13]C1(C)C)=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[NH2:11][C@@H:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[C@@H:14]([OH:13])[CH:20]=[C:21]([CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 1

HCID 70045583ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoate

Product 1

HCID 86743952ethyl (4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-2-octenoateYield 105.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

110 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoate was dissolved in 1.0 ml of ethanol, and hydrogenated by using 12 mg of 10% palladium carbon as catalyst at room temperature under atmospheric pressure. The catalyst was filtered off, and the solvent was distilled off under reduced pressure to obtain 77 mg of ethyl (4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-2-octenoate as a colorless oily substance.

Workup

  1. customat room temperature
  2. filtrationThe catalyst was filtered off
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2e22187bc4624a32946576d162b8acc8
Source dataset
uspto-grants-1990_05
Patent number
US04927565

Reaction notes

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