홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Dicyclohexylcarbodiimide → 4,4,4-Trifluoro-3-methyl-but-2-enoic acid {2-[5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propyl}-amide

HRID 1638228
노트
인쇄 미리보기

반응식

HRID 1638228 반응식
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:16][CH2:15][CH2:14][C@@:13]2([CH3:17])[C@H:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]2[C@H:18]([CH3:21])[CH2:19][NH2:20])([CH3:4])([CH3:3])[CH3:2].[F:24][C:25]([F:34])([F:33])[C:26](O)([CH3:31])[CH2:27][C:28](O)=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][CH:7]1[CH2:16][CH2:15][CH2:14][C:13]2([CH3:17])[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]2[CH:18]([CH3:21])[CH2:19][NH:20][C:28](=[O:29])[CH:27]=[C:26]([CH3:31])[C:25]([F:34])([F:33])[F:24])([CH3:3])([CH3:4])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 1361684,4,4-Trifluoro-3-hydroxy-3-methylbutanoic acidHCID 57261774(S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propylamine

생성물 1

HCID 572977674,4,4-Trifluoro-3-methyl-but-2-enoic acid {2-[5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propyl}-amide수율 15.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

701 mg (2.06 mmol) of (S)-2-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propylamine, 532 mg (1.5 eq.) of rac-3-trifluoromethyl-3-hydroxy-butyric acid, and 50 mg (0.2 eq.) of DMAP (N,N-dimethylaminopyridine) were dissolved in 20 ml of CH2Cl2. At 0° 680 mg (1.6 eq.) of DCC (dicyclohexylcarbodiimide) was added and the mixture allowed to react for 4 h at ambient temperature. The precipitated urea was filtered off and the filtrate evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=85/15) yielded in the less polar fractions 149 mg of unwanted 4,4,4-trifluoro-3-methyl-but-2-enoic acid {2-[5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-propyl}-amide and in the more polar ones 811 mg of the title compound as colorless oil. Medium pressure chromatography of the latter (SiO2, hexane/AcOEt=90/10) gave in the less polar fractions 367 mg of the (R)-butyramide and in the more polar ones 314 mg of the (S)-isomer, both as white foam. For determination of abs. configuration see d] below.

후처리

  1. customto react for 4 h at ambient temperature
  2. filtrationThe precipitated urea was filtered off
  3. customthe filtrate evaporated to dryness

출처 및 근거

ORD 기록
ord-f1c1bda672b6400799a9ee377935f238
출처 데이터셋
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06043385

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트