Tributylphosphine → 3-{4-[2-(4-Chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester

HRID 2384905ノート

反応式

HRID 2384905 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[S:23][C:24]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)=[CH:25][C:26]=3[CH2:27][CH2:28]O)=[O:21])=[CH:15][C:14]=2[O:37][CH3:38])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(P(CCCC)CCCC)CCC.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:28][CH2:27][C:26]4[CH:25]=[C:24]([C:30]5[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=5)[S:23][C:22]=4[C:20]3=[O:21])=[CH:15][C:14]=2[O:37][CH3:38])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 13831TributylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 689523253-(4-{[5-(4-Chloro-phenyl)-3-(2-hydroxy-ethyl)-thiophene-2-carbonyl]-amino}-2-methoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 689491773-{4-[2-(4-Chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester収率 67.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Dissolve 3-(4-{[5-(4-chloro-phenyl)-3-(2-hydroxy-ethyl)-thiophene-2-carbonyl]-amino}-2-methoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (840 mg, 1.50 mmol) and tri-n-butylphosphine (2.25 mmol, 562 μL) in tetrahydrofuran (15 mL) and add slowly dropwise diisopropyl azodicarboxylate (2.25 mmol, 447 μL). Stir the mixture overnight and concentrate in vacuo. Triturate the residue with Et2O, filter, and dry in vacuo to afford 550 mg (62%) of the title compound as a white solid. LC-MS/ES m/z (35Cl) 441.0 [M-tBuCO2+H]+.

後処理

  1. concentrationconcentrate in vacuo
  2. customTriturate the residue with Et2O
  3. filtrationfilter
  4. customdry in vacuo

出典と根拠

ORDレコード
ord-3217c36b1167486e9c194166e7e54bcc
出典データセット
uspto-grants-2012_09
特許番号
US08263772B2

反応ノート

読み込み中…