Phenoxyacetyl chloride → HCID 66683724, compound

HRID 579196Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[N:10]1[C:15](=[O:16])[CH2:14][CH:13]([NH2:17])[CH2:12][CH:11]1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:4].[O:30]([CH2:37][C:38](Cl)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:8][C:9]=1[N:10]1[C:15](=[O:16])[CH2:14][CH:13]([NH:17][C:38](=[O:39])[CH2:37][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:12][CH:11]1[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(4-amino-2-cyclohexyl-6-oxo-piperidin-1-yl)-5-phenyl-thiophene-2-carboxylic acid methyl ester (30 mg, 0.073 mmol, 1.0 equiv) in DCM (1.0 mL) at 0° C. was added phenoxyacetyl chloride (0.02 ml, 0.145 mmol, 2.0 equiv) and TEA (0.02 mL). The resulting mixture was then stirred at 0° C. for 20 minutes after which the solvent was removed under vacuum. The residue was purified by silica gel column chromatography (EtOAc/hepatane 10%˜80%) to give product (20 mg). MS: 547 [M+H+].)

Workup

customwas removed under vacuum
customThe residue was purified by silica gel column chromatography (EtOAc/hepatane 10%˜80%)

Sources & evidence

ORD record: ord-b07d1a42b02b40c4a144ea5125cfdb59
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040690B2

Reaction notes

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