Triphenylphosphine → HCID 59497299、化合物

HRID 1747351ノート

反応式

HRID 1747351 の反応式
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15].[C:17]([Si:21]([CH3:36])([CH3:35])[O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29]([CH2:33]O)=[CH:28][CH:27]=[CH:26]2)([CH3:20])([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:33][C:29]2[C:30]3[C:25](=[CH:24][C:23]([O:22][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:36])[CH3:35])=[CH:32][CH:31]=3)[CH:26]=[CH:27][CH:28]=2)[C:7]1=[O:15]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59497358HCID 59497358、化合物HCID 59497482HCID 59497482、化合物

生成物 1

HCID 59497299HCID 59497299、化合物収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (180 mg, 0.82 mmol) in THF (12 ml) was added [6-(tert-butyl-dimethyl-silanyloxy)-naphthalen-1-yl]-methanol (283 mg, 0.98 mmol) and triphenylphosphine (257 mg, 0.98 mmol). The DIAD (0.20 ml, 0.98 mmol) was then introduced in a dropwise manner and the resulting mixture was stirred at ambient temperature over night. Silica gel was added and the reaction mixture was concentrated to dryness. The resulting solid was purified via column chromatography (silica gel, 40% ethyl acetate/hexanes) to give 240 mg (60%) of the desired product as an oil which solidified on standing.

後処理

  1. additionSilica gel was added
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customThe resulting solid was purified via column chromatography (silica gel, 40% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-3540f009fddf428abe1addc9cf843668
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

反応ノート

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