Acetyl chloride → HCID 19390806, compound

HRID 1756707Notes

Reaction equation

HRID 1756707 reaction equation
[C:1]([NH:4][C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]([NH:15][CH:16]([CH:28]([CH3:30])[CH3:29])[CH:17]([OH:27])[C:18]([F:26])([F:25])[C:19](=[O:24])[NH:20][CH2:21][CH2:22][CH3:23])=[O:14])[C:8]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)C>O1CCCC1.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[C:10](=[O:11])[N:9]([CH2:12][C:13]([NH:15][CH:16]([CH:28]([CH3:30])[CH3:29])[C:17](=[O:27])[C:18]([F:26])([F:25])[C:19](=[O:24])[NH:20][CH2:21][CH2:22][CH3:23])=[O:14])[C:8]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[N:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 19390790HCID 19390790, compound

Product 1

HCID 19390806HCID 19390806, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(5-Acetylamino-6-oxo-2-phenyl-1,6-dihydropyrimidin-1-yl)-N-[3,3-difluoro-2-hydroxy-1-isopropyl-3-(N-propylcarbamoyl)propyl]acetamide. To a solution of the product from Example 8.a. (0.23 g) in tetrahydrofuran (5 mL) was added triethylamine (0.08 mL). Acetyl chloride (0.04 g) was added, resulting in gas evolution and precipitate formation. After 1 hour, additional triethylamine (0.04 mL) and acetyl chloride (0.02 mL) were added. After 15 minutes, the reaction was diluted with ethyl acetate and washed with water. The aqueous phase was made basic with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried. Evaporation gave a material which solidified upon further evaporation from dichloromethane:hexane. The solid (0.313 g) was not further purified; TLC: Rf =0.19, methanol:dichloromethane (5:95); 300 MHz NMR: 2.15 (s,3), 7.87 (d,1), 8.34 (t,1), 8.82 (s,1), 9.54 (s,1); MS: m/z=508 (M+1).

Workup

  1. customresulting in gas evolution and precipitate formation
  2. waitAfter 15 minutes
  3. washwashed with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. customEvaporation
  8. customgave a material which
  9. customsolidified upon further evaporation from dichloromethane

Sources & evidence

ORD record
ord-2e0d5fe8924a4de18457badd112c949a
Source dataset
uspto-grants-1995_08
Patent number
US05441960

Reaction notes

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