Tetrabutylammonium Fluoride → (S)-tert-butyl 1-hydroxybut-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

HRID 627259Notes

Reaction equation

HRID 627259 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:13]([CH2:21][C:22]([N:24]([O:26][CH3:27])[CH3:25])=[O:23])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:11]=[CH2:12])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][C@@H:10]([N:13]([CH2:21][C:22]([N:24]([O:26][CH3:27])[CH3:25])=[O:23])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89855339(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate2×

Product 1

HCID 117940379(S)-tert-butyl 1-hydroxybut-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamateYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (Intermediate 5, 10.7 g, 26.58 mmol) in THF (25 mL) was added TBAF (31.9 mL, 31.89 mmol) at 0° C. After 1 hour the reaction mixture was concentrated and purified by silica gel chromatography (hexanes/ethyl acetate) to afford the product as a light yellow oil (5.9 g, 77%).

Workup

  1. concentrationAfter 1 hour the reaction mixture was concentrated
  2. custompurified by silica gel chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-ffa08721d7424137998f88c1ed50ec3c
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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