Isopropanol → 2-Chloro-N-[3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]acetamide

HRID 843379Notes

Reaction equation

[O:1]1[CH:3]([CH:4]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][CH3:20])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:2]1.C([N:23](CC)CC)C.[Cl:28][CH2:29][C:30](Cl)=[O:31].C(O)(C)C>C(=O)(OC)OC>[Cl:28][CH2:29][C:30]([NH:23][CH2:2][CH:3]([OH:1])[CH:4]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH3:20])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:31]

Participants

Conditions

Temperature: 8 °C

Procedure

(2RS,3RS)-1,2-Epoxy-3-(2-ethoxyphenoxy)-3-phenylpropane (47.7 g) and dimethyl carbonate (700 mL) were stirred to form a white slurry. Triethylamine (52 mL) was added and the mixture cooled to 6-10° C. using an ice/H2O bath, a solution of chloroacetyl chloride (13.8 mL) in dimethyl carbonate (50 mL) was added over a 30 minute period keeping the temperature between 4-10° C. The mixture was stirred for 1 hour. The mixture was washed with 500 mL of H2O and then with 500 mL of 3% aqueous NaCl solution. The organic layer was concentrated under vacuum at 40° C. to yield a dark oil. Isopropanol (500 mL) was added and the mixture again concentrated to remove any residual dimethyl carbonate, yielding the title compound.

Workup

customto form a white slurry
custombetween 4-10° C
washThe mixture was washed with 500 mL of H2O
concentrationThe organic layer was concentrated under vacuum at 40° C.
customto yield a dark oil
concentrationthe mixture again concentrated
customto remove any residual dimethyl carbonate

Sources & evidence

ORD record: ord-9cb710f5eed9488fb4a3359463b99a2c
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376711B1

Reaction notes

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