Acetic Acid → 33605-76-4

HRID 1834758Notes

Reaction equation

HRID 1834758 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:9](=[O:10])[O:8][C:6](=[O:7])[CH2:5]1)=[O:2].C(O)(=O)C.[CH3:15][O:16][C:17](=[O:27])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:19]>C(C(C)=O)C>[CH3:15][O:16][C:17](=[O:27])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:19][C:9](=[O:10])[C@H:4]([CH2:5][C:6](=[O:7])[OH:8])[NH:3][CH:1]=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 736234L-Phenylalanine, methyl esterHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Product 1

HCID 1026805633605-76-4

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

14.3 g of N-formyl-L-aspartic anhydride (0.1 mole) was added to a mixture of 100 ml of methyl ethyl ketone and 24.0 g of acetic acid (0.4 mole). The solution was stirred at room temperature for 15 minutes. A solution of 17.9 g of L-phenylalanine methyl ester (0.1 mole) dissolved in 200 ml of methyl ethyl ketone was added to the above solution and stirred at room temperature for 6 hours to produce N-formyl-α-L-aspartyl-L-phenylalanine methyl ester.

Workup

  1. additionwas added to the above solution
  2. stirringstirred at room temperature for 6 hours

Sources & evidence

ORD record
ord-af91f728f7ff450d82eb09a5fbd98cac
Source dataset
uspto-grants-1978_01
Patent number
US04071511

Reaction notes

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