HCID 86757538, compound → HCID 86757537, compound

HRID 382346Notes

Reaction equation

HRID 382346 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([CH2:18][OH:19])=[C:13]([CH2:16][OH:17])[CH:14]=2)[C@H:9]([N:20]([CH2:25][C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])[CH2:8][C@@H:7]1[CH3:40])=[O:5])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:18][O:19][C:16](=[O:17])[C:13]=3[CH:14]=2)[C@H:9]([N:20]([CH2:25][C:26]2[CH:27]=[C:28]([C:36]([F:37])([F:39])[F:38])[CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=2)[C:21]([O:23][CH3:24])=[O:22])[CH2:8][C@@H:7]1[CH3:40])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 86757538HCID 86757538, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86757537HCID 86757537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-bis-hydroxymethyl-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 27A) (100 mg, 0.17 mmol) in 25 ml anhydrous dichloromethane was added pyridinium chloro-chromate (100 mg, 0.46 mmol) and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was poured into a separatory funnel, washed with H2O and sat NaHCO3, dried and concentrated. The crude material was chromatographed on silica gel (30-35% ethyl acetate:hexane) to afford cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-8-oxo-3,4,6,8-tetrahydro-2H-furo[3,4-g]quinoline-1-carboxylic acid ethyl ester (Example 29) MS m/z 574 (M+); 1H NMR (CDCl3) δ3.8 (s, 3H), 7.5 (s, 1H), 7.8 (s, 1H) and cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-6-oxo-3,4,6,8-tetrahydro-2H-furo[3,4-g]quinoline-1-carboxylic acid ethyl ester (Example 30) MS m/z 575 (M+); 1H NMR (CDCl3) δ1.1 (d, 3H), 3.8 (s, 3H), 7.0 (s, 1H), 8.0 (br, 1H).

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. washwashed with H2O
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was chromatographed on silica gel (30-35% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-299a26fea3ef471fb09437797eeca1b7
Source dataset
uspto-grants-2001_10
Patent number
US06310075B1

Reaction notes

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