Hydrochloric Acid → N-(Benzyloxycarbonyl)-3-amino-1,2-propanediol

HRID 1761368Notes

Reaction equation

HRID 1761368 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[OH-].[Na+].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].Cl>O.CCOCC>[CH2:13]([O:12][C:10]([NH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediol

Product 1

HCID 3362144N-(Benzyloxycarbonyl)-3-amino-1,2-propanediolYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

1-Amino-2,3-propanediol (15.2 g, 167 mmol) and NaOH (8.1 g, 204 mmol) in water (70 mL) at -10° C. was treated dropwise with benzyl chloroformate (28.5 mL, 200 mmol) in ether (30 mL) over 20 min. The reaction was stirred at 0° C. for 30 min then at room temperature for 2 h. The mixture was acidified with 2M HCl and extracted with ethyl acetate which was wash with 0.5M H3PO4 and brine, then dried over Na2SO4 and evaporated. Recrystallization of the residue from benzene afforded 16.59 g (44%) of the desired product as a white powder. NMR (300 MHz, CD3OD, ppm) 3.12 (dd,1H), 3.28 (dd,1H), 3.50 (m,2H), 3.68 (m,1H), 5.08 (s,2H), 7.35 (m,5H).

Workup

  1. waitat room temperature for 2 h
  2. extractionextracted with ethyl acetate which
  3. washwas wash with 0.5M H3PO4 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customRecrystallization of the residue from benzene

Sources & evidence

ORD record
ord-1597abe1ea1a44298ca88803164f7eff
Source dataset
uspto-grants-1989_05
Patent number
US04826815

Reaction notes

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