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 2384905Notes

Reaction equation

HRID 2384905 reaction equation
[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]

Participants

5

Reactant 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

Product 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 esterYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-3217c36b1167486e9c194166e7e54bcc
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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