Acetic Acid → HCID 10546105, compound

HRID 1277413Notes

Reaction equation

HRID 1277413 reaction equation
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:10]([NH:12][NH2:13])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:24](O)(=[O:26])[CH3:25]>C1COCC1>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:10]([NH:12][NH:13][C:24]([CH3:25])=[O:26])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 7120247N-[(Phenylmethoxy)carbonyl]-L-phenylalanine hydrazide

Product 1

HCID 10546105HCID 10546105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of THF is dissolved 2.0 g of Z-Phe-NHNH2, followed by adding 1.4 ml of anhydrous acetic acid and 0.9 ml of TEA under ice-cooling, and the mixture is stirred for 2 hours at room temperature. The precipitated crystals are collected by filtration, washed well with diethyl ether and recrystallized from ethyl acetate to give 1.9 g of crystals, m.p. 205°-206° C., [α]D23 -16.4° (c=0.50, DMF), Rf1 =0.60.

Workup

  1. temperaturecooling
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed well with diethyl ether
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ca38c6ee9a6e4193895b8f7216fa854b
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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