Acetic Anhydride → HCID 54510168, compound

HRID 614768Notes

Reaction equation

HRID 614768 reaction equation
Cl.[CH2:2]([O:9][C@H:10]([CH3:38])[C@@H:11]([C:13]([NH:15][C@H:16]([C:20]([NH:22][C@H:23]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OC(=O)C)(=O)C>C(O)(=O)C>[CH2:2]([O:9][C@H:10]([CH3:38])[C@@H:11]([C:13]([NH:15][C@H:16]([C:20]([NH:22][C@H:23]([C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70611940HCID 70611940, compound

Product 1

HCID 54510168HCID 54510168, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Benzyl O-benzylthreonylvalylleucinate is prepared from 1 gram of benzyl O-benzylthreonylvalylleucinate hydrochloride as in Example 5 and is dissolved in acetic acid, and 2 equivalents acetic anhydride based on the benzyl ester are added. The mixture is stirred overnight. The solvents are evacuated in vacuo. The residue is recrystallized from methanol/ether, to yield 806 milligrams of benzyl N-α-acetyl-O-benzylthreonylvalylleucinate (85% yield).

Workup

  1. additionare added
  2. customThe solvents are evacuated in vacuo
  3. customThe residue is recrystallized from methanol/ether

Sources & evidence

ORD record
ord-ba573c72a2f94e53bef588f5c32b5dc4
Source dataset
uspto-grants-1979_03
Patent number
US04146614

Reaction notes

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