HCID 13839325, compound → HCID 14836042, compound

HRID 1088541Notes

Reaction equation

HRID 1088541 reaction equation
[CH2:1]([O:3][C:4]([N:6]=C=NC(C)(C)C)=[O:5])[CH3:2].[F:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:28][CH3:29])[C:20]=2[C:24]([F:27])([F:26])[F:25])[C:15]=1[C:30]([N:32]([CH3:37])[CH2:33][C:34]([OH:36])=O)=[O:31]>C1COCC1>[CH2:1]([O:3][C:4]([NH:6][C:34](=[O:36])[CH2:33][N:32]([CH3:37])[C:30]([C:15]1[C:16]2[C:21](=[C:20]([C:24]([F:27])([F:25])[F:26])[C:19]([O:28][CH3:29])=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[F:13])=[O:31])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 13839325HCID 13839325, compoundHCID 14836041HCID 14836041, compound

Product 1

HCID 14836042HCID 14836042, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure of O. M. Mitsunobu et al, Bull. Chem. Soc. Japan, 45, 3607 (1972), a solution of ethoxycarbonyl-t-butylcarbodiimide (0.436, 1.10 q) and N-[[2-fluoro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-methylglycine (0.838 g, 2.38 mmole) in anhydrous THF (13.5 mL) was heated to reflux under a dry nitrogen atmosphere for 10 hours. The reaction was cooled to room temperature and the organic solvent was removed. The solid was flash chromatographed (1:1 pertroleum ether:ethyl acetate, silica). The resultant foam was triturated with petroleum ether and dried to provide the title compound as a white solid (0.567 g, 50%), m.p. 130°-132° C.

Workup

  1. temperatureto reflux under a dry nitrogen atmosphere for 10 hours
  2. customthe organic solvent was removed
  3. customchromatographed (1:1 pertroleum ether:ethyl acetate, silica)
  4. customThe resultant foam was triturated with petroleum ether
  5. customdried

Sources & evidence

ORD record
ord-2b34fb07cdaf43a4a44f544f525817de
Source dataset
uspto-grants-1990_10
Patent number
US04962224

Reaction notes

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