Triethylamine → N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]glycine, 1,1-Dimethylethyl Ester

HRID 620358Notes

Reaction equation

HRID 620358 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NOCC.[CH3:24][O:25][C:26]1[C:27]([C:45]([F:48])([F:47])[F:46])=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32]([C:36](O)=[O:37])=[C:31]([O:39][CH2:40][C:41]([F:44])([F:43])[F:42])[CH:30]=[CH:29]2.Cl.[NH2:50][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53].C(N(CC)CC)C>CN(C)C=O.O>[CH3:24][O:25][C:26]1[C:27]([C:45]([F:46])([F:47])[F:48])=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32]([C:36]([NH:50][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[O:37])=[C:31]([O:39][CH2:40][C:41]([F:42])([F:43])[F:44])[CH:30]=[CH:29]2

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 156149586-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)naphthoic acidHCID 221697771-(3-Dimethylaminopropyl)-3-ethoxycarbodiimide hydrochloride

Product 1

HCID 15614967N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]glycine, 1,1-Dimethylethyl EsterYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (4.27 g, 1.5 eq) and 1-(3-dimethylaminopropyl)-3-ethoxycarbodiimide hydrochloride (4.84 g, 1.2 eq), were added to a stirred solution of 6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)naphthoic acid (7.75 g, 21.0 mmol, prepared by the process of Example 11, Step 3) in anhydrous dimethylformamide (135 mL) under a dry nitrogen atmosphere at room temperature. After 11/4 hours, glycine, t-butyl ester hydrochloride (7.06 g, 2.0 eq) and anhydrous triethylamine (9.68 mL, 3.3 eq) were added. After another 2 hours, the reaction mixture was diluted with water (1.5 L) and extracted with ether (4×200 mL). The extracts were combined and the ether was removed. The crude product was flash chromatographed (7:3 petroleum ether:ethyl acetate, silica) to provide the title compound as a white solid (7.39 g, 73%), m.p. 146°-174.5° C.

Workup

  1. extractionextracted with ether (4×200 mL)
  2. customthe ether was removed
  3. customchromatographed (7:3 petroleum ether:ethyl acetate, silica)

Sources & evidence

ORD record
ord-6c991254672b438baf212dcfc5dc532f
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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