Chloroacetyl chloride → HCID 51357134, compound
Reaction equation
[C:1]1([CH2:7][NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:20][C:21](Cl)=[O:22].[OH-].[Na+]>C1COCC1.O>[CH3:12][C@H:9]1[N:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:21](=[O:22])[CH2:20][O:11][CH2:10]1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To (2R)-2-[(phenylmethyl)amino]-1-propanol (8.43 g, 51 mmol) in THF (50 mL) was added a solution of K2CO3 (21.15 g, 153 mmol) in water (50 mL). To the resulting mixture at 0° C. was added slowly via syringe chloroacetyl chloride (5.7 mL, 71.4 mmol) with vigorous stirring, and the reaction mixture was stirred for 1 hour at 0° C. A 50% aqueous NaOH solution was added to adjust the pH>13, and the resulting mixture was warmed up overnight to room temperature. The solution was extracted with CH2Cl2 (2×200 mL), and the organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound (100% crude yield) as a colorless oil. LC-MS (ES) m/z=206 [M+H]+
Workup
- temperaturethe resulting mixture was warmed up overnight to room temperature
- extractionThe solution was extracted with CH2Cl2 (2×200 mL)
- dry with materialthe organic layer was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4794dea112c843cdae8bc22091af8b2b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697685B2
Reaction notes
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