Acetyl chloride → HCID 67507539, compound

HRID 1791962Notes

Reaction equation

HRID 1791962 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=2)[CH2:10][C@H:9]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.Cl.C(C1C=CC(NCCN[C@@H]2CN[C@H:49]([C:52](N3CCSC3)=[O:53])C2)=NC=1)#N.C(Cl)(=O)C.C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[C:52]([N:13]([C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@H:9]([C:25]([N:27]2[CH2:31][CH2:30][S:29][CH2:28]2)=[O:26])[CH2:10]1)[CH2:14][CH2:15][NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=1)(=[O:53])[CH3:49]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 67506854HCID 67506854, compoundHCID 67507244HCID 67507244, compound

Product 1

HCID 67507539HCID 67507539, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

3-{(2S,4S)-1-tert-Butoxycarbonyl-4-{2-[(5-cyano-2-pyridyl)amino]ethyl}amino-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 319 (1), 800 mg] and triethylamine (0.42 mL) were dissolved in dichloromethane (20 mL), and acetyl chloride (0.18 mL) was added thereto under ice-cooling. The mixture was stirred at room temperature for 5 hr. The reaction mixture was added to saturated aqueous sodium hydrogencarbonate solution and the mixture was extracted with chloroform. The extract was washed with brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 3-[(2S,4S)-4-(N-acetyl-N-{2-[(5-cyano-2-pyridyl)amino]ethyl}amino)-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl]-1,3-thiazolidine (786 mg) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9aa6435213864e11a89093531e131a22
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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