Acetic Anhydride → (R)-{1-[8-Acetyl-3-(4-ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 2223145Notes

Reaction equation

HRID 2223145 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]([C:10]1[N:11]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=2)[C:12](=[O:20])[C:13]2[CH2:19][CH2:18][CH2:17][NH:16][C:14]=2[N:15]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>>[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([C:10]1[N:11]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH3:29])=[CH:25][CH:26]=2)[C:12](=[O:20])[C:13]2[CH2:19][CH2:18][CH2:17][N:16]([C:40](=[O:42])[CH3:41])[C:14]=2[N:15]=1)[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 69201576{1-[3-(4-Ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 58617397(R)-{1-[8-Acetyl-3-(4-ethoxy-phenyl)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-2-yl]-ethyl}-carbamic acid tert-butyl ester

Conditions

Temperature
80 °C

Procedure

D2 (263 mg, 0.63 mmol) and N,N-diisopropylethylamine (111 μL, 0.63 mmol) were dissolved in acetic anhydride (10 mL) and heated to 80° C. The reaction stirred overnight. It was quenched with saturated aqueous sodium bicarbonate, then extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, then dried over magnesium sulfate, filtered, concentrated in vacuo. Purified by chromatography (1:1 to 1:2 hexane:ethyl acetate), recovering 168 mg of D3.

Workup

  1. customIt was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurified by chromatography (1:1 to 1:2 hexane:ethyl acetate)
  8. customrecovering 168 mg of D3

Sources & evidence

ORD record
ord-1a61ea1a48d44e53921c65fe078abba8
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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