Sodium Hydroxide → HCID 86757535, compound

HRID 382345Notes

Reaction equation

HRID 382345 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([CH2:18]Br)=[C:13]([CH2:16]Br)[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].[OH-:41].[Na+]>C1C=CC=CC=1.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:18][O:41][CH2:16][C:13]=3[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]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86757536HCID 86757536, compound

Product 1

HCID 86757535HCID 86757535, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 159952Benzyltributylammonium chlorideCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-bis-bromomethyl-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 27B) (50 mg, 0.71 mmol) in 0.25 ml benzene was added benzyl tri-n-butylammonium chloride (23 mg, 0.71 mmol) and 30% NaOH (28 μl). The reaction mixture was heated to 80° C. for 4 hours. The mixture was diluted with 0.75 ml ethyl acetate. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (2×0.25 ml). The combined extracts were dried (MgSO4), filtered and concentrated. The crude material was chromatographed on silica gel (25% ethyl acetate:hexane) to afford the title product (10 mg, 25%). MS m/z 561 (M+); 1H NMR (CDCl3) δ3.85 (s, 3H), 6.85 (s, 1H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×0.25 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was chromatographed on silica gel (25% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-ddb99661343144829adeba8704780959
Source dataset
uspto-grants-2001_10
Patent number
US06310075B1

Reaction notes

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