Water → HCID 21277439, compound

HRID 2292317Notes

Reaction equation

HRID 2292317 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[C:16]2[C:15]([CH3:18])([CH3:17])[CH2:14][CH2:13][C:12]([CH3:20])([CH3:19])[C:11]=2[CH:10]=[C:9]([O:21][CH3:22])[C:8]=1/[CH:23]=[CH:24]/[C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.C(N(CC)CC)C.O>O1CCCC1>[C:1]([NH:30][CH2:29][C:28]1[CH:27]=[CH:26][C:25](/[CH:24]=[CH:23]/[C:8]2[C:9]([O:21][CH3:22])=[CH:10][C:11]3[C:12]([CH3:19])([CH3:20])[CH2:13][CH2:14][C:15]([CH3:18])([CH3:17])[C:16]=3[C:7]=2[O:6][CH3:5])=[CH:32][CH:31]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21277457HCID 21277457, compound

Product 1

HCID 21277439HCID 21277439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 ml of acetyl chloride in 5 ml of absolute tetrahydrofuran was added dropwise, at 20° C., to a solution of 3 g (8 millimoles) of the benzylamine derivative from Example 30, 1.6 g (16 millimoles) of triethylamine and 50 mg of DMAP (4-N,N-dimethylaminopyridine) in 25 ml of absolute tetrahydrofuran. After 1 hour at 0° C., the mixture was poured onto 100 ml of water and extracted with methylene chloride. The organic phase was dried and evaporated down, and the oily residue was heated with heptane. The mixture was cooled, the supernatant heptane phase was decanted, and the process was repeated several times. Finally, 0.8 g of the title compound of melting point 126°-127° C. crystallized out from the heptane solution and was filtered off under suction.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase was dried
  3. customevaporated down
  4. temperaturethe oily residue was heated with heptane
  5. temperatureThe mixture was cooled
  6. customthe supernatant heptane phase was decanted
  7. customFinally, 0.8 g of the title compound of melting point 126°-127° C. crystallized out from the heptane solution
  8. filtrationwas filtered off under suction

Sources & evidence

ORD record
ord-a07adb65a3d14d4aaf22c6c4629bad4a
Source dataset
uspto-grants-1989_01
Patent number
US04801733

Reaction notes

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