Trifluoroacetic acid → HCID 178454946, 화합물

HRID 1881046노트

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HRID 1881046 반응식
[C:1](O)(C(F)(F)F)=[O:2].[Cl:8][C:9]1[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=1[CH2:11][O:12][CH2:13][CH2:14][NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([CH3:22])[CH2:18][CH2:17]1.C([O:29][C:30](=[O:42])[C:31]([CH3:41])([CH3:40])[CH2:32][S:33][C:34]1[S:38][C:37]([NH2:39])=[N:36][CH:35]=1)C.C1N=CN(C(N2C=NC=C2)=O)C=1.[OH-].[Na+]>C1COCC1.CN(C1C=CN=CC=1)C.C(O)C>[Cl:8][C:9]1[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=1[CH2:11][O:12][CH2:13][CH2:14][N:15]([C@H:16]1[CH2:17][CH2:18][C@H:19]([CH3:22])[CH2:20][CH2:21]1)[C:1](=[O:2])[NH:39][C:37]1[S:38][C:34]([S:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]([OH:29])=[O:42])=[CH:35][N:36]=1

참가 물질

9

반응물 5

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 574814293-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl esterHCID 178461337HCID 178461337, 화합물

생성물 1

HCID 178454946HCID 178454946, 화합물수율 53%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

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온도
75 °C

실험 절차

The TFA salt of [2-(2-chloro-benzyloxy)-ethyl]-(trans-4-methyl-cyclohexyl)-amine (169 mg, 0.60 mmol) in THF (5 mL) was added 3-(2-amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid ethyl ester (195 mg, 0.75 mmol), CDI (243 mg, 1.50 mmol) and DMAP (3.7 mg, 0.03 mmol). The reaction mixture was stirred for 18 h. Ethanol (1 mL) and NaOH (2.5 N, 3 mL, 7.5 mmol) was added and the reaction mixture was heated to 75° C. for 5 h. The mixture was allowed to cool to rt before pH was adjusted (pH<1). The precipitate was filtered off and purified by preparative HPLC to give 170 mg (53%) of 3-{2-[3-[2-(2-Chloro-benzyloxy)-ethyl]-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-2,2-dimethyl-propionic acid.

후처리

  1. temperatureto cool to rt before pH
  2. filtrationThe precipitate was filtered off
  3. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-b4f1b506071e4047b667a6c928c06c02
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318778B2

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