Acetic Anhydride → (3-Acetylaminobenzyl-(2(S)-benzoylamino-3-methylbutyryl)-amino)acetic Acid Ethyl Ester

HRID 1456672Notes

Reaction equation

HRID 1456672 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]([C:15](=[O:29])[C@@H:16]([NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:17]([CH3:19])[CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)[CH3:2].[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1.CCOC(C)=O.Cl>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:31](=[O:33])[CH3:32])[CH:9]=1)[C:15](=[O:29])[C@@H:16]([NH:20][C:21](=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH:17]([CH3:19])[CH3:18])[CH3:2]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 54307894((2(S)-Benzoylamino-3-methylbutyryl)-(3-aminobenzyl)amino)acetic Acid Ethyl Ester

Product 1

HCID 54473761(3-Acetylaminobenzyl-(2(S)-benzoylamino-3-methylbutyryl)-amino)acetic Acid Ethyl EsterYield 99.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 735 (435.0 mg, 1.06 mmol) in pyridine (3.0 ml) was added acetic anhydride (50 μL, 1.59 mmol) and the reaction allowed to stir overnight. The reaction was diluted with EtOAc and 1N HCl. The layers were separated and the organic phase washed with brine, dried over MgSO4, filtered and concentrated to dryness to provide 480 mg of 742. ##STR121##

Workup

  1. customThe layers were separated
  2. washthe organic phase washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0451eac278324ef18f36b4d04a3a383d
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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