Ethanol → HCID 86755997, compound

HRID 279381Notes

Reaction equation

HRID 279381 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([N:19]([CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH2:8][C@@H:7]1[CH3:39])=[O:5])[CH3:2].[C:40]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:41]=1.C(O)C.CN1CCNCC1NC(N=NC(NC1CNCCN1C)=O)=O>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:40][CH3:41])=[C:13]([O:16][CH3:17])[CH:14]=2)[C@H:9]([N:19]([CH2:24][C:25]2[CH:26]=[C:27]([C:35]([F:36])([F:38])[F:37])[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=2)[C:20]([O:22][CH3:23])=[O:21])[CH2:8][C@@H:7]1[CH3:39])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 86755995HCID 86755995, compoundHCID 131722135HCID 131722135, compound

Product 1

HCID 86755997HCID 86755997, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-hydroxy-7-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (30 mg, 0.053 mmol), triphenylphosphine (28 mg, 0.11 mmol), ethanol (16 μL, 0.79 mmol), and bis-(N-methylpiperazinyl)-azodicarboxamide (30 mg, 0.11 mmol) in benzene (1 mL) was stirred at room temperature for 12 hours. Purification of the solution directly by silica gel chromatography using 0-20% ethyl acetate/hexanes as eluent afforded 20 mg of the title compound (67%): MS m/z 593 (M+), 610 (M++17); 1H NMR (CDCl3) δ6.39 (C5, s, 1H), 1.17 (C2-Me, d, 3H, J=6.2 Hz).

Workup

  1. customPurification of the solution directly by silica gel chromatography

Sources & evidence

ORD record
ord-486d5615dd9b4ab18b0f57e96bf9985b
Source dataset
uspto-grants-2002_03
Patent number
US06362198B1

Reaction notes

Loading…