Chloroacetyl chloride → HCID 66973053, compound

HRID 1367149Notes

Reaction equation

HRID 1367149 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[CH:6]=1)[CH2:3][OH:4].C(N(CC)CC)C.[Cl:20][CH2:21][C:22](Cl)=[O:23]>C(Cl)Cl>[Cl:20][CH2:21][C:22]([NH:1][C@H:2]([C:5]1[CH:6]=[C:7]([F:12])[CH:8]=[C:9]([F:11])[CH:10]=1)[CH2:3][OH:4])=[O:23]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66513514HCID 66513514, compound

Product 1

HCID 66973053HCID 66973053, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-amino-2-(3,5-difluorophenyl)ethanol from Step B (630 mg, 3.64 mmol) and triethylamine (0.51 mL, 3.64 mmol) in CH2Cl2 (40 mL) at 0° C. was added chloroacetyl chloride (0.29 mL, 3.64 mmol). After 20 min, the reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL) and extracted with CH2Cl2 (2×25 mL). The combined organic extracts were washed with 10% citric acid, then brine, then dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=250 (M+1).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL)
  2. extractionextracted with CH2Cl2 (2×25 mL)
  3. washThe combined organic extracts were washed with 10% citric acid
  4. dry with materialbrine, then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1cd1f11911742228bc7e2770c592c1b
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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