1,1'-(Diazomethylene)bis(benzene) → N-t-butoxycarbonyl DL-homoserine benzhydryl ester

HRID 2231984Notes

Reaction equation

HRID 2231984 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([OH:15])=[O:14])[CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1([C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N+]=[N-])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[CH:22]([O:14][C:13](=[O:15])[CH:9]([CH2:10][CH2:11][OH:12])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 41186272-(((Tert-butoxy)carbonyl)amino)-4-hydroxybutanoic acid

Product 1

HCID 13066458N-t-butoxycarbonyl DL-homoserine benzhydryl esterYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6 g of the obtained N-t-butoxycarbonyl DL-homoserine was dissolved in 100 ml of methylene chloride, and 50 ml of a methylene chloride solution containing 6 g of diphenyldiazomethane was added dropwise thereto over an hour. After completion of the reaction, the reaction mixture was concentrated to a small volume, and petroleum ether was added thereto. The formed crystals were filtered off to obtain 8.6 g of N-t-butoxycarbonyl DL-homoserine benzhydryl ester.

Workup

  1. additionwas added dropwise
  2. waitover an hour
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated to a small volume, and petroleum ether
  5. additionwas added
  6. filtrationThe formed crystals were filtered off

Sources & evidence

ORD record
ord-0db094c08a004530b12a9276bab5ae27
Source dataset
uspto-grants-1988_11
Patent number
US04785090

Reaction notes

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