Acetyl chloride → HCID 14403357, compound

HRID 1032682Notes

Reaction equation

HRID 1032682 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([N:8]2[CH2:15][CH:14]3[CH2:16][CH:10]([CH2:11][N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:13]3)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:26](Cl)(=[O:28])[CH3:27].C(N(CC)CC)C>O1CCCC1>[NH:1]([C:2]1[CH:25]=[CH:24][C:5]([C:6]([N:8]2[CH2:15][CH:14]3[CH2:16][CH:10]([CH2:11][N:12]([CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:13]3)[CH2:9]2)=[O:7])=[CH:4][CH:3]=1)[C:26]([CH3:27])=[O:28]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 71270Ambasilide

Product 1

HCID 14403357HCID 14403357, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

80.2 g (0.24 mole) of 3-(4-aminobenzoyl)-7-benzyl-3,7-diazabicyclo[3.3.1]nonane (cf. European Pat. No. 62,199) were dissolved in 500 ml anhydrous tetrahydrofuran and cooled with ice. 23.5 g (0.3 mole) of acetyl chloride, dissolved in 50 ml of tetrahydrofuran, were added dropwise, followed by 48.6 g (0.48 mole) of triethylamine at room temperature. The entire mixture was stirred overnight and then evaporated down under reduced pressure. The residue was taken up in water and the solution was extracted 3 times with methylene chloride. The combined organic phases were washed with water, dried and evaporated down under reduced pressure. Yield: 78.1 g, mp.: 208° C.

Workup

  1. temperaturecooled with ice
  2. additionwere added dropwise
  3. customevaporated down under reduced pressure
  4. extractionthe solution was extracted 3 times with methylene chloride
  5. washThe combined organic phases were washed with water
  6. customdried
  7. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-5ce2eea8a91a4cb4b47ac8ca99c5fe34
Source dataset
uspto-grants-1990_09
Patent number
US04959373

Reaction notes

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