Fluoride Ion → 3-[N-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

HRID 863330Notes

Reaction equation

HRID 863330 reaction equation
[CH2:1]([NH:5][C:6](=[O:51])[C@H:7]([CH2:47][CH:48]=[CH:49][CH3:50])[CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:10]1[CH2:23][C:24]([CH3:46])([CH3:45])[CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:2][CH2:3][CH3:4].[F-]>O1CCCC1.C(OCC)C>[CH2:1]([NH:5][C:6](=[O:51])[C@H:7]([CH2:47][CH:48]=[CH:49][CH3:50])[CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@H:10]1[CH2:23][C:24]([CH3:46])([CH3:45])[CH2:25][CH2:26][OH:27])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 28179Fluoride IonHCID 1317205373-[N-tert-butoxycarbonyl-4(S)-(4-tert-butyl-diphenylsilyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

Product 1

HCID 867521183-[N-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

474 mg of 3-[N-tert-butoxycarbonyl-4(S)-(4-tert-butyl-diphenylsilyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide are dissolved in 5 ml of tetrahydrofuran, and 1.2 ml of a 1M tetraburylammonium fluoride solution in tetrahydrofuran are added at room temperature under argon. After 4 h, the reaction mixture is diluted with diethyl ether, washed with water and brine, dried (Na2SO4) and concentrated. Purification over silica gel (mobile phase A) gives the title compound: Rf (A)=0.40; FAB-MS: (M+H)+ =483.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification over silica gel (mobile phase A)

Sources & evidence

ORD record
ord-01128038956347b085b5ca02052fbe56
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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