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

HRID 1088543노트

반응식

HRID 1088543 반응식
[OH:1]N1C2C=CC=CC=2N=N1.[CH3:11][N:12]([CH3:21])[CH2:13][CH2:14][CH2:15]N=C=NCC.[CH3:22][O:23][C:24]1[C:25]([C:43]([F:46])([F:45])[F:44])=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](C(O)=O)=[C:29]([O:37][CH2:38][C:39]([F:42])([F:41])[F:40])C=C2.Cl.N(C[C:51]([O:53][CH3:54])=[O:52])C.C(N(CC)CC)C>CN(C=O)C.O>[CH3:22][O:23][C:24]1[C:25]([C:43]([F:44])([F:45])[F:46])=[C:26]2[C:15](=[CH:32][CH:33]=1)[C:14]([C:13]([N:12]([CH3:11])[CH2:21][C:51]([O:53][CH3:54])=[O:52])=[O:1])=[C:29]([O:37][CH2:38][C:39]([F:40])([F:41])[F:42])[CH:30]=[CH:31]2

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 156149586-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)naphthoic acid

생성물 1

HCID 14836049N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, Methyl Ester수율 81%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

1-Hydroxybenzotriazole (5.05 g, 1.5 eq) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (5.74 g, 1.2 eq) were added to a stirred solution of 6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)naphthoic acid, prepared by the process of Example 14 (9.18 g, 24.9 mmol) in anhydrous DMF (90 mL) at room temperature under a dry nitrogen atmosphere. After 11/4 hours, a suspension of methyl sarcosinate hydrochloride (6.96 g, 2.0 eq) in anhydrous DMF (40 mL) was added to the reaction followed by triethylamine (11.12 mL, 3.2 eq). After 30 minutes, the reaction was diluted with water (1.5 L) and extracted with ether (3×250 mL). The extracts were combined, dried with magnesium sulfate, and the ether was removed. The crude product was flash chromatographed (13:7→1:1 petroleum ether:ethyl acetate, silica) to provide the product as a clear oil (9.15 g, 81%). A small sample was triturated in petroleum ether to provide a white solid for analysis, m.p. 91.5°-93° C.

후처리

  1. additionwas added to the reaction
  2. extractionextracted with ether (3×250 mL)
  3. dry with materialdried with magnesium sulfate
  4. customthe ether was removed
  5. customchromatographed (13:7→1:1 petroleum ether:ethyl acetate, silica)

출처 및 근거

ORD 기록
ord-99e891fa06cb46d49f9fe9e62ee0261b
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04962224

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