Triethylamine → 2-chloro-N-[2-(1,3-dioxolan-2-yl)ethyl]-3-phenylmethoxypropanamide

HRID 266020Notes

Reaction equation

[Cl:1][CH:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](Cl)=[O:4].[NH2:15][CH2:16][CH2:17][CH:18]1[O:22][CH2:21][CH2:20][O:19]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:1][CH:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([NH:15][CH2:16][CH2:17][CH:18]1[O:22][CH2:21][CH2:20][O:19]1)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 69.63 g of 2-chloro-3-(phenylmethoxy)propanoyl chloride (prepared according to the procedure described in Inorg. Chem., 31. 2422, 1992) (0.299 mol) in 90 ml of CHCl3 was added to a solution of 35.49 g of 2-(2-aminoethyl)-1,3-dioxolane (prepared according to the procedure described in EXAMPLE 4) (0.303 mol) and to 60.3 g of triethylamine (83 ml; 0.596 mol) in 100 ml of CHCl3 under inert atmosphere, keeping the temperature at 0°-5° C. The reaction mixture was stirred for 5 h at 25° C., then was washed with H2O. The organic phase was dried and evaporated to dryness, the residue was purified by flash chromatography. 61.68 g of the desired product (0.197 mol) were obtained.

Workup

customprepared
customat 0°-5° C
washwas washed with H2O
customThe organic phase was dried
customevaporated to dryness
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-f5360b948d974112a64ca06a0337290c
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05649537

Reaction notes

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