Dichloromethane → HCID 11225567, compound

HRID 458409Notes

Reaction equation

HRID 458409 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:28]2[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=2)[C:8]2[C:23](=[O:24])[N:22]3[CH2:25][CH2:26][CH2:27][N:21]3[C:9]=2[NH:10][C:11]=1[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:5])[CH3:2].C(Cl)Cl>C(#N)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:35][CH:36]=2)=[C:8]2[C:23](=[O:24])[N:22]3[CH2:25][CH2:26][CH2:27][N:21]3[C:9]2=[N:10][C:11]=1[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 11283254HCID 11283254, compound

Product 1

HCID 11225567HCID 11225567, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

A solution of ceric ammonium nitrate (228 mg, 0.42 mmol) in acetonitrile (1 mL) and water (0.2 mL) was added dropwise to a solution of the product from Step D (102 mg, 0.21 mmol) in acetonitrile (1 mL). The resulting solution was stirred at rt for 2 h and then concentrated at reduced pressure. Trituration of the remaining material with a mixture of CH2Cl2 and water provided E as a light yellow solid (75 mg, 0.15 mmol, 73%): 1H NMR (400 MHz, DMSO-d6) δ 13.05 (br, 1H), 7.95 (d, 2H, J=8), 7.41 (d, 2H, J=8), 7.22 (dd, 2H, J=8, 6), 7.07 (t, 2H, J˜9), 3.87 (m, 4H), 3.77 (t, 2H, J=7), 3.07 (m, 2H), 2.99 (m, 2H), 2.54 (quint., 2H, J=7), 0.75 (t, 3H, J=7) ppm; ESI-MS m/z 490 (M+H)+.

Workup

  1. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-4a063cb6e6ec4cdcbe036f664ab8d243
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

Loading…