N-Methylaniline → (2R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((6R,7S,8R,8aS)-7-acetamido-2-phenyl-8-(2-(tritylthio)acetoxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)propanoic acid

HRID 2410212노트

반응식

HRID 2410212 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:26][O:27][C@@H:28]3[O:37][CH:36]4[C@@H:31]([O:32][CH:33]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[O:34][CH2:35]4)[C@H:30]([O:44][C:45](=[O:67])[CH2:46][S:47][C:48]([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C@@H:29]3[NH:68][C:69](=[O:71])[CH3:70])[C:20]([O:22]CC=C)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CNC1C=CC=CC=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:26][O:27][C@@H:28]3[O:37][CH:36]4[C@@H:31]([O:32][CH:33]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[O:34][CH2:35]4)[C@H:30]([O:44][C:45](=[O:67])[CH2:46][S:47][C:48]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)[C@@H:29]3[NH:68][C:69](=[O:71])[CH3:70])[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 7515N-MethylanilineHCID 86651901(2R)-allyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((6R,7S,8R,8aS)-7-acetamido-2-phenyl-8-(2-(tritylthio)acetoxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)propanoate

생성물 1

HCID 86651903(2R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((6R,7S,8R,8aS)-7-acetamido-2-phenyl-8-(2-(tritylthio)acetoxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yloxy)propanoic acid수율 95%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

Allyl protected glycosyl amino acid 34 (135 mg, 0.14 mmol) was suspended in THF (6 ml). N-methylaniline (0.15 ml, 1.38 mmol) and Pd(PPh3)4 (16 mg, 0.01 mmol) were added and the reaction stirred at rt for 20 min. The solvent was removed in vacuo and the product purified by column chromatography (eluent: 95:5 v/v dichloromethane/methanol—9:1 v/v dichloromethane/methanol) to give the desired acid 35 as a pale yellow solid (123 mg, 95%).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe product purified by column chromatography (eluent: 95:5 v/v dichloromethane/methanol—9:1 v/v dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-381569df18ee4b8f87eea61e60c50b0c
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816050B2

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