1-Octanol → HCID 86755990, compound

HRID 370047Notes

Reaction equation

HRID 370047 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:59](O)[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66].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:17][CH3:18])=[C:13]([O:16][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH:14]=2)[C@H:9]([N:19]([CH2:24][C:25]2[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[C:27]([C:35]([F:36])([F:38])[F:37])[CH:26]=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 9571-OctanolHCID 11776TriphenylphosphineHCID 86755988HCID 86755988, compoundHCID 131722135HCID 131722135, compound

Product 1

HCID 86755990HCID 86755990, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (30 mg, 0.053 mmol), triphenylphosphine (28 mg, 0.11 mmol), 1-octanol (33 μL, 0.21 mmol), and bis-(N-methylpiperazinyl)-azodicarboxamide (30 mg, 0.11 mmol) in benzene (1 mL) was stirred at room temperature for 2 days. Purification of the solution directly by silica gel chromatography using 0-20% ethyl acetate/hexanes as eluent afforded the title compound (18 mg, 50%). MS m/z 695 (M+ +19), 376 (M+ -300); 1H NMR (CDCl3) δ 7.08 (C8, s, 1H), 6.40 (C5, s, 1H), 1.17 (C2-Me, d, 3H, J=6.1 Hz).

Workup

  1. customPurification of the solution directly by silica gel chromatography

Sources & evidence

ORD record
ord-bc5f11a61ad54bbb841f560971b6a91e
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

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