Tributylphosphine → HCID 57501761, compound

HRID 601525Notes

Reaction equation

HRID 601525 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:26])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([O:24][CH3:25])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.C(OC([N:34]1[CH2:39][CH2:38][O:37][CH:36]([CH2:40]O)[CH2:35]1)=O)(C)(C)C.P(CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:26])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:40][CH:36]5[O:37][CH2:38][CH2:39][NH:34][CH2:35]5)=[C:19]([O:24][CH3:25])[CH:18]=4)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylateHCID 57501754HCID 57501754, compound

Product 1

HCID 57501761HCID 57501761, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2-(4-chloro-phenyl)-5-(4-hydroxy-3-methoxy-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (103 mg, 0.267 mmol), 2-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester (Pharmacore, CAS: 135065-69-9) (70 mg, 0.324 mmol), and PBu3 (84 μl, 0.324 mmol) in dry toluene (1.2 mL). Cool to 0° C. then add 1,1′-(azodicarbonyl)piperidine (84 μl, 0.324 mmol). Let stir for 10 min at 0° C., then warm to ambient temperature overnight. Reaction mixture thickens and turns gel like. Add hexanes and collect solid via vacuum filtration. Wash the solid with hexanes several times. Dissolve the crude material in dry CH2Cl2 (500 μL) and TFA (200 μl) and stir overnight. Add 1N NaOH until the reaction is pH=10 and extract with EtOAc (3×10 mL). Dry the combined organic portions with Na2SO4, filter, and concentrate to give the title compound. MS (ES+) 486.0 (M+1)+.

Workup

  1. temperaturewarm to ambient temperature overnight
  2. customReaction mixture thickens
  3. customAdd hexanes and collect solid
  4. filtrationvia vacuum filtration
  5. washWash the solid with hexanes several times
  6. dissolutionDissolve the crude material in dry CH2Cl2 (500 μL) and TFA (200 μl)
  7. stirringstir overnight
  8. additionAdd 1N NaOH until the reaction
  9. extractionextract with EtOAc (3×10 mL)
  10. dry with materialDry the combined organic portions with Na2SO4
  11. filtrationfilter
  12. concentrationconcentrate

Sources & evidence

ORD record
ord-11fe1e42637c4ae5b0c9b21163a260bc
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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