Triethylamine → HCID 66973514, compound

HRID 1367173Notes

Reaction equation

HRID 1367173 reaction equation
[C:1]1([C@H:7]([CH2:9][OH:10])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:18][CH:19]([CH2:23][CH3:24])[C:20](Cl)=[O:21]>C(Cl)Cl>[Cl:18][CH:19]([CH2:23][CH3:24])[C:20]([NH:8][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:9][OH:10])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1390532-Chlorobutanoyl chlorideHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 66973514HCID 66973514, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-phenylglycinol (2.00 g, 14.6 mmol) and triethylamine (2.03 mL, 14.6 mmol) in CH2Cl2 (100 mL) at 0° C. was slowly added 2-chlorobutyryl chloride (1.66 mL, 14.6 mmol). After 30 min, the reaction mixture was quenched with saturated aqueous NaHCO3 (30 mL) and extracted with CH2Cl2 (2×75 mL). The combined organic extracts were washed with 10% citric acid, then brine, then 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=242 (M+1).

Workup

  1. customat 0° C.
  2. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (30 mL)
  3. extractionextracted with CH2Cl2 (2×75 mL)
  4. washThe combined organic extracts were washed with 10% citric acid
  5. dry with materialbrine, then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-17606c9f898743ac91cff9b01ab6e0a6
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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