Allyl bromide → (S)-3-(Allyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

HRID 627588Notes

Reaction equation

[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[H-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C=O)C>[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][O:4][CH2:19][CH:18]=[CH2:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of Boc-Ser-OH (21.5 g, 0.105 mol) in DMF at 0° C. was added sodium hydride (8.4 g, 0.21 mol). The reaction mixture was stirred at 0° C. for 15 mins, and then allyl bromide (13.3 g, 0.105 mol) was added. The mixture was stirred at 40° C. overnight. After TLC showed the reaction was completed, the mixture was quenched with aqueous NH4Cl solution and concentrated in vacuum. The residue was diluted with water, and sequentially washed with hexane and ether. The organic layers were discarded, and the aqueous layer was carefully adjusted to pH=3 with 1 N HCl. The acidic aqueous solution was extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated in vacuum to give Boc-Ser(O-allyl)-OH (14.0 g, 54.4%).

Workup

stirringThe mixture was stirred at 40° C. overnight
customthe mixture was quenched with aqueous NH4Cl solution
concentrationconcentrated in vacuum
additionThe residue was diluted with water
washsequentially washed with hexane and ether
extractionThe acidic aqueous solution was extracted with ethyl acetate
washThe organic phase was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuum

Sources & evidence

ORD record: ord-3da36718986e4cf993fbe517f4409e47
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309285B2

Reaction notes

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