Tri-o-tolylphosphine → HCID 178418607, 화합물

HRID 6529

반응식

HRID 6529 반응식
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]=[CH:10][N:11]1[C:16]([OH:17])=[C:15]2[CH:18]=[C:19]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[N:20]=[C:14]2[N:13]=[CH:12]1.I[C:29]1[CH:50]=[CH:49][C:32]([C:33]([NH:35][C@H:36]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:34])=[CH:31][CH:30]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.IC1C=CC(C(N[C@H](C(OCC)=O)CCC([O-])=O)=O)=CC=1>C(N(CC)CC)C.C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]([C:29]1[CH:50]=[CH:49][C:32]([C:33]([NH:35][C@H:36]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:34])=[CH:31][CH:30]=1)=[CH:10][N:11]1[C:16]([OH:17])=[C:15]2[CH:18]=[C:19]([NH:21][C:22](=[O:27])[C:23]([CH3:24])([CH3:26])[CH3:25])[N:20]=[C:14]2[N:13]=[CH:12]1

참가 물질

8

반응물 4

HCID 80271Tri-o-tolylphosphineHCID 1885228diethyl (2S)-2-[(4-iodobenzoyl)amino]pentanedioateHCID 86747251ethyl N-(4-iodobenzoyl)glutamateHCID 178418674HCID 178418674, 화합물

생성물 1

HCID 178418607HCID 178418607, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

A mixture containing 3.48 g of 3-(3-tetrahydropyr-2-yloxyprop-1-en-1-yl)-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine, 3.12g (1.2 equiv.) of diethyl N-(4-iodobenzoyl)glutamate, 546 mg (20%) of tris-(2-methylphenyl)phosphine, 201 mg (10%) of palladium acetate and 85.5 mg (5%) of cuprous iodide in 15 ml of triethylamine and 240 ml of acetonitrile is heated at reflux under nitrogen. After 12 hours., 1.17 g of ethyl N-(4-iodobenzoyl)glutamate are added and the reaction mixture is heated at reflux under nitrogen for an additional 12 hours. The reaction mixture then is concentrated under reduced pressure and the residue chromatographed on silica gel, eluting with 20:1 ethyl acetate:hexane. (Any recovered starting material can be recycled through the foregoing procedure.) The concentrated material is dissolved in 1:5 ethyl acetate:ether and this solution is refrigerated for 15 hours. The solid which forms is collected by filtration, washed with cold ethyl acetate and dried to yield diethyl N-[4-{1-(tetrahydropyr-2-yloxy)-3-(4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidin-3-yl)prop-2-en-2yl}benzoyl]glutamate.

후처리

  1. temperatureis heated
  2. temperatureat reflux under nitrogen
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux under nitrogen for an additional 12 hours
  5. concentrationThe reaction mixture then is concentrated under reduced pressure
  6. customthe residue chromatographed on silica gel
  7. washeluting with 20:1 ethyl acetate
  8. dissolution) The concentrated material is dissolved in 1:5 ethyl acetate
  9. waitether and this solution is refrigerated for 15 hours
  10. filtrationThe solid which forms is collected by filtration
  11. washwashed with cold ethyl acetate
  12. customdried

출처 및 근거

ORD 기록
ord-f4b94ff8ba9e4c06ac8d51b313e46253
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248775

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