Water → HCID 86756031, compound

HRID 1937470Notes

Reaction equation

HRID 1937470 reaction equation
[CH3:1][S-:2].[Na+].[CH2:4]([O:6][C:7]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH2:19]Br)[CH:17]=2)[C@H:12]([N:23]([CH2:28][C:29]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=2)[C:24]([O:26][CH3:27])=[O:25])[CH2:11][C@@H:10]1[CH3:43])=[O:8])[CH3:5].O>CN(C)C=O>[CH2:4]([O:6][C:7]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH2:19][S:2][CH3:1])[CH:17]=2)[C@H:12]([N:23]([CH2:28][C:29]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=2)[C:24]([O:26][CH3:27])=[O:25])[CH2:11][C@@H:10]1[CH3:43])=[O:8])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 86756032HCID 86756032, compound

Product 1

HCID 86756031HCID 86756031, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium thiomethoxide (11 mg, 0.156 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-7-bromomethyl-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 90) (100 mg, 0.156 mmol), and the reaction was stirred for 6 h. The reaction mixture was then poured into water and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The excess N,N-dimethylformamide was azeotroped off with heptanes. Purification by silica gel chromatography using 10-15% ethyl acetate/hexanes as eluent afforded the title product (0.040 g, 42%): 1H NMR (CDCl3) δ 1.1 (d, 3H), 2.1 (s, 3H), 3.8 (m, 6H), 6.4 (s, 1H), 7.3 (s, 1H), 7.7 (s, 2H), 7.8 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe excess N,N-dimethylformamide was azeotroped off with heptanes
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-85775da71612423a956f1bbf1c8fc48e
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

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