Ammonia → HCID 57186127, compound

HRID 1738676Notes

Reaction equation

HRID 1738676 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH2:26][C:27]3[O:28][C:29]4[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:30]=4[CH:31]=3)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C.C=O.C(Cl)(Cl)Cl.N>C(O)=O>[C:36]([C:33]1[CH:34]=[CH:35][C:29]2[O:28][C:27]([CH2:26][CH:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][C@H:10]4[CH2:11][CH2:12][N:8]([CH3:6])[CH2:9]4)=[CH:15][CH:16]=3)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:31][C:30]=2[CH:32]=1)#[N:37]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 6212ChloroformHCID 10323852ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate

Product 1

HCID 57186127HCID 57186127, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

1.8 g of ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)propionate was dissolved in 28 ml of formic acid, and the solution was stirred at 70° C. for 1 hour. The resulting reaction solution was concentrated to dryness, and the residue thus obtained was dissolved in 8 ml of formic acid. 0.29 ml of 37% formaldehyde was added thereto, and then refluxed under heating for 4 hours. After cooling, the reaction solution was mixed with chloroform, and then adjusted to pH 10-11 with aqueous ammonia, and the resulting organic layer was collected and dried. Thereafter, the solvent was distilled off, and the resulting residue was purified by silica gel column chromatography using a chloroform/methanol mixture as an eluant. In this way, 1.07 g of the title compound was obtained in an oily form.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated to dryness
  3. customthe residue thus obtained
  4. temperaturerefluxed
  5. temperatureunder heating for 4 hours
  6. temperatureAfter cooling
  7. customthe resulting organic layer was collected
  8. customdried
  9. distillationThereafter, the solvent was distilled off
  10. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d950844109cf471e83f03ab354488acb
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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