Hydrochloric Acid → HCID 54334607, compound

HRID 583404Notes

Reaction equation

HRID 583404 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6](Cl)=[O:7].C(N(CC)CC)C.C([O:27][C:28](=[O:44])[CH2:29][CH:30]([NH:42][CH3:43])[CH2:31][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=1)C.[OH-].[Na+].Cl>COC(C)(C)C.CO>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([N:42]([CH:30]([CH2:31][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=1)[CH2:29][C:28]([OH:44])=[O:27])[CH3:43])=[O:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 53825613HCID 53825613, compound

Product 1

HCID 54334607HCID 54334607, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

25.3 g (91.4 mmol) of 3,5-bistrifluoromethyl-benzoyl chloride followed by 13.3 ml (95.6 mmol) of triethylamine are added dropwise over a period of 5 minutes to a solution of 22.5 g (83.1 mmol) of 3-methylamino-4-(2-naphthyl)-butanoic acid ethyl ester in 500 ml of tert-butyl methyl ether. After 12 hours at room temperature, 16.6 g (415 mmol) of sodium hydroxide dissolved in 150 ml of methanol are added over a period of 10 minutes and the mixture is stirred for 5 hours. Then, at 0° C., 275 ml of 2N hydrochloric acid are added and the mixture is washed with 300 ml of ethyl acetate. After concentration in a rotary evaporator, the title compound crystallises out from tert-butyl methyl ether/hexane in the form of white needles. M.p.: 128-130° C.; IR: 3400-2500 (b), 1710, 1635 cm1 ; 1H-NMR, 200 MHz, CDCl3, delta, (ppm): 7.9-6.93 (m, 10H), 5.01, 4.30 (2m, rotamer, 1H), 3.9-2.6 (m, 4H), 3.18, 2.68 (2s, rotamer, 3H).

Workup

  1. additionare added over a period of 10 minutes
  2. washthe mixture is washed with 300 ml of ethyl acetate
  3. concentrationAfter concentration
  4. customin a rotary evaporator
  5. customthe title compound crystallises out from tert-butyl methyl ether/hexane in the form of white needles

Sources & evidence

ORD record
ord-6bc70ad17e0840adb388b673e4cd962a
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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