Hydrochloric Acid → 2-(4-Nitrobenzyloxycarbonyl)amino-1,3-propanediol

HRID 846938

Reaction equation

[OH:1][CH2:2][C@H:3]([NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)=[O:10])[C:4](OC)=[O:5].[BH4-].[Na+].Cl.O>O1CCCC1.C(O)C.C(OCC)(=O)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:11][C:9]([NH:8][CH:3]([CH2:4][OH:5])[CH2:2][OH:1])=[O:10])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl (2S)-3-hydroxy-2-[(4-nitrobenzyloxycarbonyl)amino]propionate (2.12 g) in tetrahydrofuran (20 ml) and ethanol (20 ml) was added sodium borohydride(0.54 g) at 0° C. under nitrogen atmosphere. After stirring at 0° C. for 5 hours, to the mixture was added a mixture of concentrated hydrochloric acid (1.7 ml), water (40 ml) and ethyl acetate (40 ml). The organic layer was separated, washed with 10% aqueous sodium hydrogen carbonate and brine successively, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (160 ml) eluting with a mixture of acetone and dichloromethane (1:9, V/V) to give 2-[(4-nitrobenzyloxycarbonyl)amino]-1,3-propanediol (1.32 g).

Workup

additionwas added
customThe organic layer was separated
washwashed with 10% aqueous sodium hydrogen carbonate and brine successively
dry with materialdried over magnesium sulfate
customevaporated
customThe residue was chromatographed on silica gel (160 ml)
washeluting with a mixture of acetone and dichloromethane (1:9, V/V)

Sources & evidence

ORD record: ord-4fa55c7b31f24088824c87c674dc8b79
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05138064

Linked notes

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