Ethyl Acetate → 2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine

HRID 1975459Notes

Reaction equation

[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[CH2:10]OS(C)(=O)=O)=[O:6])[CH:2]=[CH2:3].[Cl-].[NH4+].[N-:28]=[N+]=[N-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[CH2:10][NH2:28])=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 7.00 g of 2-(N-allyloxycarbonylaminomethyl)-3-t-butyldimethylsilyloxy-1-methanesulfonyloxybutane and 1.42 g of ammonium chloride in 70 ml of N,N-dimethylformamide was added 1.73 g of sodium azide at 0° C. The mixture was stirred at 50° C. for 7 hours. After the starting material disappeared, 350 ml of ethyl acetate and 350 ml of water were added to the reaction mixture. The organic layer was washed in turn with water three times and brine. The half amount of solvent was evaporated and then 5.11 g of triphenylphosphine was added thereto portionwise. After stirring overnight, 2.15 g of 28% aqueous ammonia was added and the mixture was stirred for 8 hours, and then evaporated under reduced pressure to give 11.36 g of crude 2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine.

Workup

washThe organic layer was washed in turn with water three times and brine
customThe half amount of solvent was evaporated
addition5.11 g of triphenylphosphine was added
stirringAfter stirring overnight
addition2.15 g of 28% aqueous ammonia was added
stirringthe mixture was stirred for 8 hours
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-be3f58fd5d2448d9b1fe5f886841c916
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05286721

Reaction notes

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