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 2384905노트

반응식

HRID 2384905 반응식
[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]

참가 물질

5

반응물 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

생성물 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 ester수율 67.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-3217c36b1167486e9c194166e7e54bcc
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263772B2

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