Water → HCID 86758100, compound

HRID 1937472Notes

Reaction equation

HRID 1937472 reaction equation
C(S([O:8][N+:9]([O-])=[O:10])(=O)=O)(F)(F)F.[CH2:12]([O:14][C:15]([N:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=2)[C@H:20]([N:28]([CH2:33][C:34]2[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[C:36]([C:44]([F:47])([F:46])[F:45])[CH:35]=2)[C:29]([O:31][CH3:32])=[O:30])[CH2:19][C@@H:18]1[CH3:48])=[O:16])[CH3:13].O>ClCCl>[CH2:12]([O:14][C:15]([N:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][C:25]=2[N+:9]([O-:10])=[O:8])[C@H:20]([N:28]([CH2:33][C:34]2[CH:35]=[C:36]([C:44]([F:47])([F:45])[F:46])[CH:37]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:39]=2)[C:29]([O:31][CH3:32])=[O:30])[CH2:19][C@@H:18]1[CH3:48])=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 13161436HCID 13161436, compoundHCID 131722151HCID 131722151, compound

Product 1

HCID 86758100HCID 86758100, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a pre-dried flask under nitrogen atmosphere was prepared a slurry of F3CSO3NO2 (2.6 mmol) in 9 mL of dichloromethane [ref. J. Org. Chem. 1973, 38 (25), 4243]. The solution was cooled to −78° C. and a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-chloro-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 32) (0.72 g, 1.3 mmol) in anhydrous dichloromethane (5 mL) was added. The reaction was stirred at −78° C. for 1.5 h, then warmed to 0° C. and stirred for 1 h and 40 min. Water (30 mL) was then added, and the mixture was extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to give the title product (0.75 g, 96%). MS m/z 598 (M++H); 1H NMR (CDCl3) δ 7.85 (bs, 1H), 7.8 (bs, 1H), 7.7 (bs, 1H), 7.65 (bs, 1H), 7.1 (bs, 1H), 3.80 (s, 3H).

Workup

  1. temperaturewarmed to 0° C.
  2. stirringstirred for 1 h and 40 min
  3. extractionthe mixture was extracted three times with dichloromethane
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86f5f0b77b1b41b181d14ba419d8309c
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

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