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

1,1'-Carbonyldiimidazole → tert-butyl (4aR,7aR)-2-benzamido-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

HRID 338118
노트
인쇄 미리보기

반응식

HRID 338118 반응식
[NH2:1][C@:2]1([C:16]2[S:20][N:19]=[CH:18][CH:17]=2)[C@H:6]([CH2:7]O)[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[C:21]([N:29]=[C:30]=[S:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[C:21]([NH:29][C:30]1[S:31][CH2:7][C@@H:6]2[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][C@:2]2([C:16]2[S:20][N:19]=[CH:18][CH:17]=2)[N:1]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 68284Benzoyl isothiocyanateHCID 86762492tert-Butyl (3R,4R)-3-amino-4-(hydroxymethyl)-3-isothiazol-5-yl-pyrrolidine-1-carboxylate

생성물 1

HCID 86762226tert-butyl (4aR,7aR)-2-benzamido-7a-isothiazol-5-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

반응 조건

온도
0 °C

실험 절차

tert-Butyl (3R,4R)-3-amino-4-(hydroxymethyl)-3-isothiazol-5-yl-pyrrolidine-1-carboxylate (148.10 g, 494.67 mmol) and tetrahydrofuran (1.48 L) are added together and the solution is cooled to 0° C. Benzoyl isothiocyanate (82.34 g, 504.56 mmol) is added over 5 minutes and the reaction mixture is stirred for 30 minutes at 0° C. and then warmed to room temperature over 1 hour. 1,1′-Carbonyldiimidazole (92.24 g, 568.87 mmol) is added and the reaction mixture is stirred at room temperature for 2 h. The mixture is heated to 65° C. and stirred for a further 12 hours. The reaction mixture is concentrated under reduced pressure and the oily residue is partitioned between water (1.5 L) and ethyl acetate (1.5 L). The pH is adjusted with citric acid 50% w/w aq. solution to 4.0 and the organic layer is separated. The aqueous layer is extracted with MTBE (2×500 mL), the organics are combined, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude product is slurried in MTBE (740.50 mL) at 60° C. then at room temperature for 45 minutes. The solid is collected, washed with MTBE (4×150 mL), and dried under vacuum overnight to give the title compound as an off white solid (162.68 g, 74.0%). ES/MS (m/e): 445 (M+H), ee=99.5%.

후처리

  1. temperaturewarmed to room temperature over 1 hour
  2. stirringthe reaction mixture is stirred at room temperature for 2 h
  3. temperatureThe mixture is heated to 65° C.
  4. stirringstirred for a further 12 hours
  5. concentrationThe reaction mixture is concentrated under reduced pressure
  6. customthe oily residue is partitioned between water (1.5 L) and ethyl acetate (1.5 L)
  7. customthe organic layer is separated
  8. extractionThe aqueous layer is extracted with MTBE (2×500 mL)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customis slurried in MTBE (740.50 mL) at 60° C.
  13. waitat room temperature for 45 minutes
  14. customThe solid is collected
  15. washwashed with MTBE (4×150 mL)
  16. customdried under vacuum overnight

출처 및 근거

ORD 기록
ord-367d374593a44e7b8b44278c5c3408a8
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889856B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트