Triethylamine → HCID 66973554, compound

HRID 1866638Notes

Reaction equation

HRID 1866638 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]([CH3:23])[C:20](Cl)=[O:21]>C(Cl)Cl>[Cl:18][CH:19]([CH3:23])[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 1110192-Chloropropionyl chlorideHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 66973554HCID 66973554, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-phenylglycinol (1.00 g, 7.3 mmol) and triethylamine (1.02 mL, 7.3 mmol) in CH2Cl2 (50 mL) at 0° C. was slowly added 2-chloropropionyl chloride (0.72 mL, 7.3 mmol). After 20 min, the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL) and extracted with CH2Cl2 (2×50 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=228 (M+1).

Workup

  1. customat 0° C.
  2. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL)
  3. extractionextracted with CH2Cl2 (2×50 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

Sources & evidence

ORD record
ord-19f44691361347db944f84194810af5b
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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