2-Bromo-N-methoxy-N-methylacetamide → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

HRID 627203Notes

Reaction equation

HRID 627203 reaction equation
[Si](OC[C@@H](N)C(C)=C)(C(C)(C)C)(C)[CH3:2].BrCC(N(OC)C)=O.[Si:23]([O:30][CH2:31][C@@H:32]([N:35]([CH2:43][C:44]([N:46]([O:48][CH3:49])[CH3:47])=[O:45])[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:33]=[CH2:34])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>>[Si:23]([O:30][CH2:31][C@@H:32]([N:35]([CH2:43][C:44]([N:46]([O:48][CH3:49])[CH3:47])=[O:45])[C:36](=[O:42])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])[C:33]([CH3:2])=[CH2:34])([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:24])[CH3:25]

Participants

4

Reactant 3

HCID 108669612-Bromo-N-methoxy-N-methylacetamide2×HCID 89851469(S)-1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-amine2×HCID 89855339(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Product 1

HCID 131735288(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamateYield 39%

Procedure

The title compound was prepared from (S)-1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-amine (Intermediate 187, 5.57 g, 25.86 mmol) and 2-bromo-N-methoxy-N-methylacetamide (Intermediate 4, 4.28 g, 23.53 mmol) following the procedure described for Intermediate 5. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the desired product as a colorless oil (4.24 g, 39%).

Sources & evidence

ORD record
ord-de151e95372c4c8bb8ff9492630faaf5
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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