Acetic Anhydride → HCID 10546105, compound

HRID 1277388Notes

Reaction equation

HRID 1277388 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](OC(=O)C)(=[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 7918Acetic AnhydrideHCID 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 2.03 g (6.5 m mols) of Z-Phe-NH-NH2, and under cooling, 1.4 ml of acetic anhydride and 0.9 ml of TEA are added dropwise. The mixture is stirred at room temperature for 2 hours. The crystals are collected by filtration, washed with diethyl ether and recrystallized from AcOEt. 1.9 g (83%); m.p. 205°-206° C.; [α]D23 -16.4° (c=0.5, DMF); Rf1 =0.60.

Workup

  1. temperatureunder cooling
  2. filtrationThe crystals are collected by filtration
  3. washwashed with diethyl ether
  4. customrecrystallized from AcOEt

Sources & evidence

ORD record
ord-12ed4d196a754626be2c181784a8e164
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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