Triethylamine → HCID 66973552, compound

HRID 1864863Notes

Reaction equation

HRID 1864863 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][CH:21]([CH2:25][CH3:26])[C:22](Cl)=[O:23]>C(Cl)Cl>[Cl:20][CH:21]([CH2:25][CH3:26])[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 8471TriethylamineHCID 1390532-Chlorobutanoyl chlorideHCID 66513514HCID 66513514, compound2×

Product 1

HCID 66973552HCID 66973552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-amino-2-(3,5-difluorophenyl)ethanol (2.60 g, 15.0 mmol, described in Intermediate 10) and triethylamine (4.19 mL, 30.0 mmol) in CH2Cl2 (150 mL) at 0° C. was slowly added 2-chlorobutyryl chloride (1.71 mL, 15.0 mmol). After 60 min, the reaction mixture was quenched with saturated aqueous NaHCO3 (40 mL) and extracted with CH2Cl2 (2×100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-70:30 to 0:100, to give the title compound. MS: m/z=278 (M+1).

Workup

  1. customat 0° C.
  2. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (40 mL)
  3. extractionextracted with CH2Cl2 (2×100 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-f721971dad4d435ab4271ab286b44da5
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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