1-Hydroxybenzotriazole → Methyl 3-[2-({[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}amino)-2-oxoethyl]benzoate

HRID 227459Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:11][C:12]([OH:14])=O)[CH:8]=[CH:9][CH:10]=1)=[O:4].[Cl:15][C:16]1S[C:19]([CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH:24]([CH2:28][NH2:29])[CH2:23]2)=[CH:18][CH:17]=1.ON1C2C=CC=[CH:39][C:34]=2N=N1.[ClH:40].CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:40][C:17]1[CH:18]=[C:19]([CH:39]=[CH:34][C:16]=1[Cl:15])[CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH:24]([CH2:28][NH:29][C:12](=[O:14])[CH2:11][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])[CH2:23]1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of [3-(methoxycarbonyl)phenyl]acetic acid (0.200 g), Intermediate 1 (0.284 g), 1-hydroxybenzotriazole (0.182 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.316 g) was stirred in dichloromethane (10 ml), and N,N-diisopropylethylamine (0.352 ml) was added to the solution. Stirring at 20° C. under nitrogen was continued for 8 h. The mixture was purified by solid phase extraction (2×10 g Varian Bondelut silica gel cartridges), eluting successively with one column volume of dichloromethane, chloroform, ether, ethyl acetate, acetone, acetonitrile and methanol, to give the title compound as a colourless gum, (0.266 g).

Workup

customThe mixture was purified by solid phase extraction (2×10 g Varian Bondelut silica gel cartridges)
washeluting successively with one column volume of dichloromethane, chloroform, ether, ethyl acetate, acetone, acetonitrile and methanol

Sources & evidence

ORD record: ord-9e76dd28952e4fc99ac98cab9379cab8
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560548B2

Reaction notes

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