Chloroacetyl chloride → HCID 66972953, compound

HRID 1367154Notes

Reaction equation

HRID 1367154 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][CH2:19][C:20](Cl)=[O:21]>C(Cl)Cl>[Cl:18][CH2:19][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 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 66972953HCID 66972953, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-phenylglycinol (10 g, 73 mmol) and triethylamine (10.2 mL, 73 mmol) in CH2Cl2 (500 mL) at 0° C. was slowly added chloroacetyl chloride (5.8 mL, 73 mmol). After 20 min, the reaction mixture was quenched with saturated aqueous NaHCO3 (150 mL) and extracted with CH2Cl2 (2×250 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=214 (M+1).

Workup

  1. customat 0° C.
  2. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (150 mL)
  3. extractionextracted with CH2Cl2 (2×250 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-0690b3e600da422390d8ee5636cd935d
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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