(R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl chloride → (2R)-N-{[7-(1-Hydroxycyclopentyl)-6,7-dihydrocyclobuta[g][1]benzofuran-7-yl]methyl}-2,3-dihydro-1,4-benzodioxine-2-carboxamide

HRID 2229440Notes

Reaction equation

HRID 2229440 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11](Cl)=[O:12].[NH2:14][CH2:15][C:16]1([C:27]2([OH:32])[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:19]2[C:20]3[O:24][CH:23]=[CH:22][C:21]=3[CH:25]=[CH:26][C:18]=2[CH2:17]1>ClCCl.C(N(C(C)C)CC)(C)C.O>[OH:32][C:27]1([C:16]2([CH2:15][NH:14][C:11]([C@@H:2]3[O:1][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][CH2:3]3)=[O:12])[C:19]3[C:20]4[O:24][CH:23]=[CH:22][C:21]=4[CH:25]=[CH:26][C:18]=3[CH2:17]2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 2

HCID 7022160(R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl chlorideHCID 184677861-[7-(Aminomethyl)-6,7-dihydrocyclobuta[g][1]benzofuran-7-yl]cyclopentanol

Product 1

HCID 69953004(2R)-N-{[7-(1-Hydroxycyclopentyl)-6,7-dihydrocyclobuta[g][1]benzofuran-7-yl]methyl}-2,3-dihydro-1,4-benzodioxine-2-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 762 mg of (2R)-2,3-dihydrobenzo[1,4]dioxin-2-ylcarboxylic acid chloride is added, at 0° C., to 900 mg of the compound obtained in Step A in 30 ml of dichloromethane and 1.2 ml of diisopropylethylamine. After 48 hours at room temperature, the reaction mixture is diluted with water and extracted with dichloromethane. Conventional treatment of the organic phases enables, after evaporation under reduced pressure, the expected product to be isolated in the form of a meringue.

Workup

  1. extractionextracted with dichloromethane
  2. customafter evaporation under reduced pressure

Sources & evidence

ORD record
ord-2b032aa984264521900368960fc2444a
Source dataset
uspto-grants-2002_07
Patent number
US06420413B2

Reaction notes

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