(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamate → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamate

HRID 627204Notes

Reaction equation

HRID 627204 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:14]([CH2:22][C:23](N(OC)C)=[O:24])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([CH3:13])=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OC[C@@H](N(CC(=O)C(C)=C)C(=O)OC(C)(C)C)C=C)([C:32](C)([CH3:34])[CH3:33])(C)C.C([Mg]Br)=CC(=C)C>>[Si:1]([O:8][CH2:9][C@@H:10]([N:14]([CH2:22][C:23](=[O:24])[C:32]([CH3:34])=[CH2:33])[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[C:11]([CH3:13])=[CH2:12])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 131735276(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamateHCID 131735288(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate2×HCID 178445933HCID 178445933, compound

Product 1

HCID 131735289(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamateYield 92%

Procedure

The title compound was prepared from (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (Intermediate 188, 4.24 g, 10.18 mmol) following the procedure described for Intermediate 6 substituting the relevant isoprenyl magnesium bromide (0.5 M in THF) (204 mL, 101.77 mmol). Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the desired product as a light yellow oil (3.72 g, 92%).

Sources & evidence

ORD record
ord-e9536782d7194ad1935af978fe0a3e5e
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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