Acetic Acid → HCID 178445917, compound

HRID 464896Notes

Reaction equation

HRID 464896 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@H:37]([CH:42]=NNC(N)=O)[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:52])CCC.C(O)(=O)C>O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@H:37]([CH:42]=[O:52])[CH2:38][CH:39]([CH3:40])[CH3:41])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2631-ButanolHCID 178445904HCID 178445904, compound

Product 1

HCID 178445917HCID 178445917, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 200 mg. of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidyl-L-leucinal semicarbazone in 2 ml. of the upper layer of a 4:1:5 by volume mixture of 1-butanol, glacial acetic acid and water was subjected to partition chromatography on a Sephadex (trade mark) G-25 column (column size: 2.5 cm. inner diameter×100.5 cm. length) and eluted with the same solvent as above. Fractions coloured with Pauli's reagent and 2,4-dinitrophenylhydrazine were collected and the solvent was removed under reduced pressure from the collected fractions. When diethyl ether was added to the residue, there were obtained 96 mg. of the desired compound as a white powdery solid, melting at 106°-108° C.; [α]22 -49.0° (C=0.5, methanol).

Workup

  1. customto partition chromatography on a Sephadex (trade mark) G-25 column (column size: 2.5 cm. inner diameter×100.5 cm. length)
  2. washeluted with the same solvent as above
  3. customwere collected
  4. customthe solvent was removed under reduced pressure from the collected fractions
  5. additionWhen diethyl ether was added to the residue
  6. customthere were obtained 96 mg

Sources & evidence

ORD record
ord-eede8bfc8c5141019dc3f09a214201b0
Source dataset
uspto-grants-1985_10
Patent number
US04548926

Reaction notes

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