Oxalyl chloride → HCID 18703878, compound

HRID 399225Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To ice-cold DMF (1 ml) under an argon atmosphere was added oxalyl chloride (68 ml, 0.78 mmol). After stirring for 5 min at 0° C., a solution of (1RS,2SR,3SR)-1-(4-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxamide (150 mg, 0.39 mmol) in DMF (2 ml) was added, and stirring was continued for an additional 10 min at 0° C. The reaction mixture was partitioned between EtOAc and 3M HCl. The aqueous phase was extracted with EtOAc, and the combined organic extracts were washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo to afford the title compound as a white solid (135 mg, 94%) which was used without further purification.

Workup

stirringstirring
waitwas continued for an additional 10 min at 0° C
customThe reaction mixture was partitioned between EtOAc and 3M HCl
extractionThe aqueous phase was extracted with EtOAc
washthe combined organic extracts were washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
customdried
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-082f7c72b94d464a8347e1874c19a277
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05817693

Reaction notes

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