Glycine → N-[(Phenylmethoxy)carbonyl]-L-phenylalanylglycine

HRID 1759506Notes

Reaction equation

HRID 1759506 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[NH2:29][CH2:30][C:31]([OH:33])=[O:32].C(N(CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 750GlycineHCID 1049PyridineHCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanine2×

Product 1

HCID 6994632N-[(Phenylmethoxy)carbonyl]-L-phenylalanylglycineYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.299 g (0.001 mol) of N-benzyloxycarbonylphenylalanine (Z-Phe), 0.08 g (0.001 mol) of pyridine and 0.256 g (0.001 mol) of DSC in 10 ml of acetonitrile was stirred at ambient temperature. After silica gel TLC. showed that Z-Phe (the free acid form) disappeared in the solution, the reaction solution was admixed with 0.075 g (0.001 mol) of glycine (Gly-OH) and 0.101 g (0.001 mol) of triethylamine, followed by stirring at ambient temperature for 24 hours. The resultant reaction mixture was concentrated to a small volume, admixed with ethyl acetate, washed with aqueous 4% NaHCO3, with 1 N-HCl and with a saturated aqueous solution of sodium chloride, followed by drying over anhydrous sodium sulfate. The dried solution was filtered and the filtrate was distilled to remove the solvent, affording a colorless crystalline substance. Recrystallization of this solid substance from ethyl acetate-petroleum ether gave 0.30 g of N-benzyloxycarbonylphenylalanylglycine (Z-Phe-Gly-OH) as a colorless crystalline substance. Yield 83.4%.

Workup

  1. customThe resultant reaction mixture
  2. concentrationwas concentrated to a small volume
  3. washwashed with aqueous 4% NaHCO3, with 1 N-HCl and with a saturated aqueous solution of sodium chloride
  4. dry with materialby drying over anhydrous sodium sulfate
  5. filtrationThe dried solution was filtered
  6. distillationthe filtrate was distilled
  7. customto remove the solvent
  8. customaffording a colorless crystalline substance
  9. customRecrystallization of this solid substance from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-8433fb8f7ee540d7864716080fffdeb1
Source dataset
uspto-grants-1982_07
Patent number
US04341707

Reaction notes

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