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

Triethylamine → Methyl 4-[2-(benzotriazol-1-yloxycarbonyl)-vinyl]-benzoate

HRID 1180801
노트
인쇄 미리보기

반응식

HRID 1180801 반응식
[C:1]([CH:4]=[CH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)([OH:3])=[O:2].CCN(CC)CC.CN([P+](O[N:34]1[N:42]=[N:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[N:41]1([O:2][C:1]([CH:4]=[CH:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=2)=[O:3])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[N:42]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 86881Benzoic acid, 4-(2-carboxyethenyl)-, methyl esterHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

생성물 1

HCID 72479810Methyl 4-[2-(benzotriazol-1-yloxycarbonyl)-vinyl]-benzoate수율 84%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution at room temperature of VII (264 mg, 1.28 mmol) in anhydrous DMF (10 ml) under nitrogen were added Et3N (196 μl, 1.41 mmol) and BOP reagent (680 mg, 1.1.54 mmol), respectively. After few min, a precipitate appeared. After 3 h, the reaction mixture was poured into a saturated aqueous solution of NH4Cl, and diluted with AcOEt. After separation, the organic layer was successively washed with sat NH4Cl, H2O and brine, concentrated a little bit, and hexane was added. The suspension was filtered off and rinsed with hexane. The solid was triturated in water, filtered off, rinsed with water, and dried to afford the title compound VIII (346 mg, 1.07 mmol, 84% yield) as a pale yellow solid (not stable on silica gel !). 1H NMR (300 MHz, CDCl3) δ(ppm): 8.56 (d, J=8.3 Hz, 1H), 8.21–8.02 (m, 3H), 7.90–7.72 (m, 4H), 7.62 (t, J=7.4 Hz, 1H), 3.97 (s, 3H).

후처리

  1. customAfter separation
  2. washthe organic layer was successively washed with sat NH4Cl, H2O and brine
  3. concentrationconcentrated a little bit, and hexane
  4. additionwas added
  5. filtrationThe suspension was filtered off
  6. washrinsed with hexane
  7. customThe solid was triturated in water
  8. filtrationfiltered off
  9. washrinsed with water
  10. customdried

출처 및 근거

ORD 기록
ord-b1cd1211c3ba4805bf348d7d224f7f9b
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07282608B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트