Hydrochloric Acid → 21948-10-7

HRID 325278Notes

Reaction equation

HRID 325278 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH:10]([N:20]=[N+]=[N-])[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:24].[H][H]>C(O)C.[Re+5]=S>[ClH:24].[CH2:1]([O:8][C:9](=[O:23])[CH:10]([CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14104112HCID 14104112, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1410411521948-10-7Yield 88%

Reagents, catalysts & solvents 2

HCID 178528042HCID 178528042, compoundCatalystHCID 702EthanolSolvent

Procedure

1.56 grams (0.005 mole) of 2-azido-3-benzyloxypropionic acid benzyl ester were dissolved in 10 ml of ethanol, 1.50 grams (0.041 mole) of dry hydrogen chloride gas led in and 0.03 grams of rhenium (VII) sulfide added. This reaction mixture was hydrogenated in an autoclave for 20 hours at 25° C. and a hydrogen pressure of 20 bar. After filtering off the catalyst the solvent was vaporized. The oil obtained (1.42 grams=88% of crude O-benzyl-D,L-serine benzyl ester hydrochloride) was dissolved in chloroform and treated with diethyl ether. The precipitated crystals were recrystallized three times from ethanol/diethyl ether. There was obtained 0.78 grams (48% of theory) of O-benzyl-D,L-serine benzyl ester hydrochloride having a melting point of 144.5°-145.5° C. (literature: 147.5°-148.5° C.).

Workup

  1. additionadded
  2. filtrationAfter filtering off the catalyst the solvent

Sources & evidence

ORD record
ord-5da203cebbdb41e5baf92729ca7f8cee
Source dataset
uspto-grants-1984_04
Patent number
US04440686

Reaction notes

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