Triethylamine → HCID 16727989, compound

HRID 1596321Notes

Reaction equation

HRID 1596321 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C(N(CC)CC)C.[CH3:14][C:15]1[CH:51]=[CH:50][CH:49]=[CH:48][C:16]=1[CH2:17][NH:18][C:19]([C@@H:21]1[C:25]([CH3:27])([CH3:26])[S:24][CH2:23][N:22]1[C:28](=[O:47])[C@@H:29]([OH:46])[C@@H:30]([NH:38][C:39](=[O:45])[C@H:40]([CH:42]([CH3:44])[CH3:43])[NH2:41])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:20]>C(OCC)(=O)C>[CH3:14][C:15]1[CH:51]=[CH:50][CH:49]=[CH:48][C:16]=1[CH2:17][NH:18][C:19]([C@@H:21]1[C:25]([CH3:27])([CH3:26])[S:24][CH2:23][N:22]1[C:28](=[O:47])[C@@H:29]([OH:46])[C@@H:30]([NH:38][C:39](=[O:45])[C@@H:40]([NH:41][C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH:42]([CH3:44])[CH3:43])[CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 20686737HCID 20686737, compound

Product 1

HCID 16727989HCID 16727989, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Ethyl chloroformate (32 μel), 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 (3 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 purified using silica gel column chromatography and reprecipitated from ethyl acetate/n-hexane to obtain the title compound (149 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 purified
  5. customreprecipitated from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-1c4f103c54d24ae097d13de6fbc92c88
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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