Chloroacetyl chloride → HCID 66616092, compound

HRID 2367059Notes

Reaction equation

HRID 2367059 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.[NH2:7][C@@H:8]([CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH3:27])([CH3:26])[C:18]2=[O:28])[CH2:13][CH2:12]1)=[O:10].C(N(CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]([NH:7][C@@H:8]([CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:9]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH3:27])([CH3:26])[C:18]2=[O:28])[CH2:15][CH2:16]1)=[O:10])=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66616074HCID 66616074, compound

Product 1

HCID 66616092HCID 66616092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of chloroacetyl chloride (120 microL, 1.49 mmol) in dichloromethane (5 mL) was slowly added a mixture of (S)-1-(1-(2-amino-4-phenylbutanoyl)piperidin-4-yl)-3,3-dimethylindolin-2-one hydrochloride (600 mg, 1.36 mmol, EXAMPLE 1, Step 4) and triethylamine (420 microL, 2.99 mmol) in dichloromethane (4 mL) at 0° C. After 5 min, the reaction was quenched with water and the mixture was diluted with ethyl acetate to separate. The organic layer was washed with water (×2) and brine, dried over sodium sulfate and concentrated to give the title compound. The product was diluted with 6.0 mL of tetrahydrofuran to give 0.226 mol/L tetrahydrofuran solution assuming 100% conversion. The stock solution was used for the next step without further purification.

Workup

  1. customthe reaction was quenched with water
  2. additionthe mixture was diluted with ethyl acetate
  3. customto separate
  4. washThe organic layer was washed with water (×2) and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-863e7ee993a241beaf3da6e88dd74fba
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

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