Water → HCID 53827834, compound

HRID 1900179Notes

Reaction equation

HRID 1900179 reaction equation
CN1CCOCC1.Cl.[CH3:9][CH:10]([NH:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:25])[CH3:24])[NH2:22])[CH2:11][S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29].O>C(Cl)Cl>[CH3:9][CH:10]([NH:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:25])[CH3:24])[NH:22][C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29])[CH2:11][S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 15891Phenyl chloroformateHCID 22866838HCID 22866838, compound

Product 1

HCID 53827834HCID 53827834, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.3 g of N-methylmorpholine was added to a suspension containing 3.0 g of N1 -(1-methyl-2-phenylthioethyl)-L-valinamide hydrochloride suspended in 80 ml of methylene chloride, at -15° C. After 1.9 g of phenyl chloroformate was added to the mixture at -15° C., the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred, and was stirred for 15 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus obtaining 2.3 g of the desired product in the form of a white crystal (yield: 54%).

Workup

  1. stirringwas stirred for 15 hours at room temperature
  2. washAfter the methylene chloride layer was washed with water
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customthe methylene chloride was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-16b379ffe51e4da0877b169198d19f1d
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

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