HCID 178491487, compound → HCID 178491486, compound

HRID 133795Notes

Reaction equation

HRID 133795 reaction equation
[C:1]([NH:4][C:5]1[C:35]([Cl:36])=[CH:34][C:8]([CH2:9][NH:10]/[C:11](=[N:26]\[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])/[NH:12][C:13](=[O:25])[CH2:14][CH:15]([OH:24])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:7][C:6]=1[Cl:37])(=[O:3])[CH3:2]>ClCCl.O=[Mn]=O>[C:1]([NH:4][C:5]1[C:6]([Cl:37])=[CH:7][C:8]([CH2:9][NH:10]/[C:11](=[N:26]\[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:30])[CH3:31])/[NH:12][C:13](=[O:25])[CH2:14][C:15]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[O:24])=[CH:34][C:35]=1[Cl:36])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 178491487HCID 178491487, compound

Product 1

HCID 178491486HCID 178491486, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (E)-tert-butyl (4-acetamido-3,5-dichlorobenzylamino)(3-hydroxy-3-(4-methoxyphenyl)propanamido)methylenecarbamate (26 mg) and MnO2 in dichloromethane (0.10 mL) was stirred at 50° C. for 12 h. The crude reaction mixture was filtered and concentrated under vacuum to give the title compound as a yellow sticky oil (17 mg, 66% yield). 1H NMR (400 MHz, CDCl3) δ 1.43-1.51 (9H, m), 1.11 (3H, s), 3.76-3.90 (5H, m), 4.35-4.69 (2H, m), 6.75-7.25 (4H, m), 7.26-7.90 (3H, m), 8.70 (1H, brd s), 11.90 (1H, brd s). HPLC retention time: 2.775 min (method A). MS (ESI) (M+H)+ 551.01.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-22308959af7746babb65285b5bf2ef3e
Source dataset
uspto-grants-2008_06
Patent number
US07390925B2

Reaction notes

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