Acetic Acid → HCID 67165753, compound

HRID 553322Notes

Reaction equation

HRID 553322 reaction equation
[C:1]([O:5][C:6](=[O:32])[N:7]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][O:17]C2CCCCO2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.O.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>O1CCCC1>[C:1]([O:5][C:6](=[O:32])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][OH:17])[CH:10]=1)[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 67165503HCID 67165503, compound

Product 1

HCID 67165753HCID 67165753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-Pyridin-2-yl-ethyl)-{3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-benzyl}-carbamic acid tert-butyl ester (8 g) in tetrahydrofuran (100 mL) was treated with acetic acid (10 mL) and water (10 mL). The reaction was refluxed for 8 hour. Another 10 mL acetic and 10 mL water were added and the reaction heated at reflux for a further 2 hours. The reaction was cooled and the volatiles removed under vacuum. The reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo. The yellow residue was passed through a plug of silica, eluting with ether then ethyl acetate to elute the desired product (4.1 g).

Workup

  1. temperatureThe reaction was refluxed for 8 hour
  2. temperaturethe reaction heated
  3. temperatureat reflux for a further 2 hours
  4. temperatureThe reaction was cooled
  5. customthe volatiles removed under vacuum
  6. customThe reaction mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate
  7. dry with materialThe organic layers were dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. washeluting with ether
  10. washethyl acetate to elute the desired product (4.1 g)

Sources & evidence

ORD record
ord-41fab6042afc4e0494be9df77cc1ed62
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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