ethyl 9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(R,S)-hydroxy-7,7-dimethyl-non-2-inoate → ethyl 9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(R,S)-hydroxy-7,7-dimethyl-nonanoate

HRID 863273Notes

Reaction equation

HRID 863273 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH3:32])([CH3:31])[CH2:12][C@H:13]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:14]([OH:22])[C:15]#[C:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[Pt]>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH3:31])([CH3:32])[CH2:12][C@H:13]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:14]([OH:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 131720520ethyl 9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(R,S)-hydroxy-7,7-dimethyl-non-2-inoate

Product 1

HCID 131720519ethyl 9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(R,S)-hydroxy-7,7-dimethyl-nonanoate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.85 g of ethyl 9-benzyloxy-5(S)-tert-butoxycarbonylamino-4(R,S)-hydroxy-7,7-dimethyl-non-2-inoate in 100 ml of tetrahydrofuran is hydrogenated in the presence of 1.2 g of platinum-on-charcoal (5% of Pt; a further 1.2 g of catalyst are added after 24 h) at room temperature under normal pressure for 33 h. Filtration of the reaction mixture over Hyflo® and concentration of the filtrate gives the crude title compound as a yellow oil: Rf (B)=0.32; FAB-MS: (M+H)+ =452.

Workup

  1. filtrationFiltration of the reaction mixture over Hyflo® and concentration of the filtrate

Sources & evidence

ORD record
ord-071e8c8e070045fb892e7e0c615ad075
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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