Triethylamine → HCID 16727995, compound

HRID 1596327Notes

Reaction equation

HRID 1596327 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:13][C:14]1[CH:50]=[CH:49][CH:48]=[CH:47][C:15]=1[CH2:16][NH:17][C:18]([C@@H:20]1[C:24]([CH3:26])([CH3:25])[S:23][CH2:22][N:21]1[C:27](=[O:46])[C@@H:28]([OH:45])[C@@H:29]([NH:37][C:38](=[O:44])[C@H:39]([CH:41]([CH3:43])[CH3:42])[NH2:40])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:19].C(OCC)(=O)C>C(Cl)Cl>[CH3:13][C:14]1[CH:50]=[CH:49][CH:48]=[CH:47][C:15]=1[CH2:16][NH:17][C:18]([C@@H:20]1[C:24]([CH3:26])([CH3:25])[S:23][CH2:22][N:21]1[C:27](=[O:46])[C@@H:28]([OH:45])[C@@H:29]([NH:37][C:38](=[O:44])[C@@H:39]([NH:40][S:2]([CH3:1])(=[O:4])=[O:3])[CH:41]([CH3:43])[CH3:42])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 20686737HCID 20686737, compound

Product 1

HCID 16727995HCID 16727995, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (25 μl) and triethylamine (46 μl) were added to a solution of H-Val-Apns-Dmt-NHBzl(2-Me) (162 mg) in methylene chloride (3 ml) and the mixture was stirred for two hours. 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 (127 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-b6e0a03677054f43a843f291c2202810
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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