Ammonia → HCID 57186127, compound

HRID 361895Notes

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

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.

Workup

customThe resulting reaction solution
concentrationwas concentrated to dryness
customthe residue thus obtained
temperaturerefluxed
temperatureunder heating for 4 hours
temperatureAfter cooling
customthe resulting organic layer was collected
customdried

Sources & evidence

ORD record: ord-728a7c5598e141a6a3ddc61251e5cfbd
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866577

Reaction notes

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