Methyl chloroformate → HCID 57647082, compound

HRID 1171158Notes

Reaction equation

HRID 1171158 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH:12]=[C:13]([Cl:28])[C:14]=1[CH2:15][C@@H:16]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:17]1=[O:27].Cl[C:37]([O:39][CH3:40])=[O:38].C(N(CC)CC)C>C(Cl)Cl>[CH3:40][O:39][C:37]([N:24]1[CH2:25][CH2:26][CH:21]([N:18]2[CH2:19][CH2:20][C@@H:16]([CH2:15][C:14]3[C:13]([Cl:28])=[CH:12][C:11]([C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)=[CH:10][C:9]=3[Cl:8])[C:17]2=[O:27])[CH2:22][CH2:23]1)=[O:38]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 86629122HCID 86629122, compound

Product 1

HCID 57647082HCID 57647082, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (R)-3-(3,5-Dichloro-4′-fluoro-biphenyl-4-ylmethyl)-1-piperidin-4-yl-pyrrolidin-2-one trifluoroacetic acid (Preparation 29) (0.10 g, 0.19 mmol) in CH2Cl2 (3 mL) with methyl chloroformate (0.03 mL, 0.36 mmol) and triethylamine (0.07 mL, 0.48 mmol). Stir the reaction for 1 hr at room temperature. Quench the reaction with 1N HCl and extract with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 0.085 g (74%) of product. MS (m/e): 479 (M+1).

Workup

  1. customthe reaction for 1 hr at room temperature
  2. customQuench
  3. customthe reaction with 1N HCl
  4. extractionextract with Et2O
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Sources & evidence

ORD record
ord-6e634dc12f0347d69755954eb9419e70
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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