Acetic Acid → HCID 67040433, compound

HRID 605329Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:44])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]5[CH:39]=[CH:38][C:37]([Br:40])=[CH:36][N:35]=5)=[O:33])=[CH:27][C:26]=4[N+:41]([O-])=O)=[CH:20][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>[Fe].C(O)C>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:44])[NH:17][C:18]3[CH:19]=[CH:20][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]5[CH:39]=[CH:38][C:37]([Br:40])=[CH:36][N:35]=5)=[O:33])=[CH:27][C:26]=4[NH2:41])=[CH:22][CH:23]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The product from Example 384C (0.20 gm, 0.30 mmol) was suspended in a 4/1 v-v mixture of glacial acetic acid and ethanol (8 ml). To this vigorously stirred suspension was added, in one portion, iron powder (0.215 gm, 3.85 mmol) and the resulting mixture heated under nitrogen in an oil bath at 100° C. After 19.5 hours the reaction mixture was cooled then concentrated under vacuum to a paste which was suspended in water and the solid product collected by vacuum filtration. The cake was washed with water then dried in vacuo at room temperature (0.204 gm, quant.).

Workup

temperatureAfter 19.5 hours the reaction mixture was cooled
concentrationthen concentrated under vacuum to a paste which
filtrationthe solid product collected by vacuum filtration
washThe cake was washed with water
customthen dried in vacuo at room temperature (0.204 gm, quant.)

Sources & evidence

ORD record: ord-51218a58fa104993bd06d3b7fe479dda
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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