Triphenylphosphine → 2,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester

HRID 1747326ノート

反応式

HRID 1747326 の反応式
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24](=[O:30])[C:25]([CH3:29])([CH3:28])[CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:22][O:23][C:24](=[O:30])[C:25]([CH3:29])([CH3:28])[CH2:26][N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[C:10]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=3[S:7][CH:8]=2)[C:13]1=[O:21]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 84152Methyl 3-hydroxypivalateHCID 594973791-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

生成物 1

HCID 594976752,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (50 mg, 0.17 mmol), 3-Hydroxy-2,2-dimethyl-propionic acid methyl ester (0.026 mL, 0.20 mmol) and triphenylphosphine (53 mg, 0.20 mmol) in dry THF (1.5 mL) is added diisopropyl azodicarboxylate (0.041 mL, 0.20 mmol) in a drop wise manner. The mixture is stirred at room temperature for 40 hrs. Then the solvent is removed under vacuum and the residue is purified by two preparative TLC's (first one is developed with 30% EtOAc in Hexanes, second one is developed with 1% MeOH in CH2Cl2) to give 28 mg (41%) of 2,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester.

後処理

  1. customThen the solvent is removed under vacuum
  2. customthe residue is purified by two preparative TLC's (first one is developed with 30% EtOAc in Hexanes, second one is developed with 1% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-f8f81140dfec4f01a7d4b29f0c2ed3ab
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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