Acetic Anhydride → HCID 16727993, compound

HRID 1596325Notes

Reaction equation

HRID 1596325 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C(N(CC)CC)C.[CH3:15][C:16]1[CH:52]=[CH:51][CH:50]=[CH:49][C:17]=1[CH2:18][NH:19][C:20]([C@@H:22]1[C:26]([CH3:28])([CH3:27])[S:25][CH2:24][N:23]1[C:29](=[O:48])[C@@H:30]([OH:47])[C@@H:31]([NH:39][C:40](=[O:46])[C@H:41]([CH:43]([CH3:45])[CH3:44])[NH2:42])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:21]>C(OCC)(=O)C>[CH3:15][C:16]1[CH:52]=[CH:51][CH:50]=[CH:49][C:17]=1[CH2:18][NH:19][C:20]([C@@H:22]1[C:26]([CH3:28])([CH3:27])[S:25][CH2:24][N:23]1[C:29](=[O:48])[C@@H:30]([OH:47])[C@@H:31]([NH:39][C:40](=[O:46])[C@@H:41]([NH:42][C:5](=[O:7])[CH3:6])[CH:43]([CH3:45])[CH3:44])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 20686737HCID 20686737, compound

Product 1

HCID 16727993HCID 16727993, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Acetic anhydride (31 μl) and triethylamine (46 μl) were added to a solution of H-Val-Apns-Dmt-NHBzl(2-Me) (162 mg) obtained in the step 2 of Example 8 in ethyl acetate (5 ml) and the mixture was stirred overnight. After the addition of ethyl acetate, the reaction mixture was washed with 3% Na2CO3, 1N HCl, and 5% NaCl and dried over MgSO4. After filtration and concentration, the residue was reprecipitated from ethyl acetate/n-hexane to obtain the title compound (143 mg).

Workup

  1. washthe reaction mixture was washed with 3% Na2CO3, 1N HCl, and 5% NaCl
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was reprecipitated from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-2e5a0f96648b442bb9018b657646bfb4
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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