Acetic Anhydride → HCID 71112459, compound

HRID 1472751Notes

Reaction equation

HRID 1472751 reaction equation
[NH2:1][C:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[O:4].[C:32](OC(=O)C)(=[O:34])[CH3:33]>C(Cl)Cl>[C:32]([NH:1][C:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:9][CH2:8]1)=[O:4])(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 71093387HCID 71093387, compound2×

Product 1

HCID 71112459HCID 71112459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 4-((2-amino-2,2-diphenylacetyloxy)-methyl)piperidine-1-carboxylate (prepared as in Preparation intermediate 12 with diphenylglycine replacing cyclohexylmandelic acid) (0.50 g, 1.18 mmol) in DCM (1.5 mL) was added a solution of acetic anhydride (0.122 mL, 1.30 mmol) in DCM (0.5 mL). The reaction mixture was heated at 40° C. for 18 hours. The reaction mixture was allowed to cool to RT and further acetic anhydride (0.06 mL, 0.65 mmol) added. The reaction mixture was heated at 40° C. for a further 18 hours. The reaction mixture was allowed to cool to RT, quenched with water, and the mixture was stirred at RT for 1 hour. The reaction mixture was then partitioned between saturated aqueous sodium hydrogen carbonate and DCM. The organic phase was removed and the aqueous phase extracted with further DCM. The combined DCM extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The product was isolated (0.541 g, >100%). The crude product was used without further purification in the next step.

Workup

  1. temperatureto cool to RT
  2. temperatureThe reaction mixture was heated at 40° C. for a further 18 hours
  3. temperatureto cool to RT
  4. customquenched with water
  5. customThe reaction mixture was then partitioned between saturated aqueous sodium hydrogen carbonate and DCM
  6. customThe organic phase was removed
  7. extractionthe aqueous phase extracted with further DCM
  8. washThe combined DCM extracts were washed with brine
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe product was isolated (0.541 g, >100%)
  13. customThe crude product was used without further purification in the next step

Sources & evidence

ORD record
ord-a5a7b10718cf415fb89af713a2577256
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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