Glycine tert-butyl ester → Tert-butyl 2-{[1,3-bis(acetyloxy)propan-2-yl]amino}acetate
Reaction equation
[C:1]([O:4][CH2:5][C:6](=O)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].[NH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:9]([O:8][CH2:7][CH:6]([NH:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]Participants
Procedure
To a solution of 3-(acetyloxy)-2-oxopropyl acetate (3.0 g, 17.24 mmol) on dichloroethane (70 ml) was added tert-butyl 2-aminoacetate (2.35 ml, 17.24 mmol). The reaction was stirred for 90 minutes before sodium triacetoxyborohydride (5.5 g, 25.86 mmol) was added and stirring was continued for 18 hours. The reaction was quenched by the addition of saturated sodium hydrogen carbonate solution and the crude product was extracted into dichloromethane. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. The title compound was purified by silica column chromatography eluting with 0-40% EtOAc:Hept to yield the title compound (1.93 g, 38% yield). 1H NMR (250 MHz, CHLOROFORM-d) δ 3.96-4.26 (4H, m), 3.30-3.45 (2H, m), 3.06 (1H, quin, 5.4 Hz), 2.09 (6H, s), 1.47 (9H, s).
Workup
- additionwas added
- customThe reaction was quenched by the addition of saturated sodium hydrogen carbonate solution
- extractionthe crude product was extracted into dichloromethane
- customThe organic phase was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe title compound was purified by silica column chromatography
- washeluting with 0-40% EtOAc
Sources & evidence
- ORD record
- ord-ee187c311dc24d6b97db835572b2c9d2
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791134B2
Reaction notes
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