HCID 86648816, compound → HCID 86648815, compound

HRID 43915Notes

Reaction equation

HRID 43915 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:12][N:11](C(C2C=CC=CC=2)C2C=CC=CC=2)[C@H:10]1[CH2:26][CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:12][NH:11][C@H:10]1[CH2:26][CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86648816HCID 86648816, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86648815HCID 86648815, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (100 mg) was added to a solution of trans(±)-3-(tert-butoxycarbonyl)amino-1-(diphenylmethyl)-2-ethylazetidine obtained in Example (234d) (530 mg, 1.45 mmol) in methanol (7 mL), and the mixture was stirred in a hydrogen stream at 40° C. for 13 hours. The reaction solution was filtered, and then the filtrate was concentrated under reduced pressure. A 1 N aqueous hydrochloric acid solution was added to the resulting residue. The aqueous layer was washed with ethyl acetate, and then saturated aqueous sodium bicarbonate solution was added, followed by extraction with ethyl acetate and a chloroform/methanol mixed solvent. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. Thereafter, the filtrate was concentrated under reduced pressure to obtain 206 mg of the title compound as a white solid (71%).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionA 1 N aqueous hydrochloric acid solution was added to the resulting residue
  4. washThe aqueous layer was washed with ethyl acetate
  5. additionsaturated aqueous sodium bicarbonate solution was added
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThereafter, the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c12d7cf2f1944654b0b15a4b05e03a21
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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