HCID 19390801, compound → HCID 19390813, compound

HRID 1756711Notes

Reaction equation

HRID 1756711 reaction equation
C(OC([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:40]([CH3:42])[CH3:41])[C:24](=[O:39])[C:25]([F:38])([F:37])[C:26](=[O:36])[NH:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:21])[C:15]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N:14][CH:13]=1)=O)C1C=CC=CC=1>C(O)C.O1CCCC1.[Pd]>[NH2:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:40]([CH3:42])[CH3:41])[C:24](=[O:39])[C:25]([F:38])([F:37])[C:26](=[O:36])[NH:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:21])[C:15]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[N:14][CH:13]=1

Participants

5

Reactant 1

HCID 19390801HCID 19390801, compound

Product 1

HCID 19390813HCID 19390813, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-pyrimidin-1-yl)-N-[3,3-difluoro-1-isopropyl-2-oxo-3-[N-(tert-butoxycarbonylmethyl)carbamoyl]propyl]acetamide (0.20 g) in ethanol (1 mL) and tetrahydrofuran (2 mL) was added 10% (v/v) palladium on carbon (0.075 g), and the mixture was shaken under a hydrogen atmosphere (3 bar) for 2.5 hours. The mixture was filtered through diatomaceous earth and evaporated. Chromatography, with chloroform:methanol (96:4) as the eluent, gave material which was precipitated from dichloromethane and hexane to yield the title compound as a white solid (0.128 g); TLC: Rf =0.35, chloroform:methanol (96:4); MS: m/z=498(M+1). Analysis for C24H31F2N5O6.0.3 H2O: Calculated: C, 55.51; H, 5.89; N, 12.95; Found: C, 55.65; H, 5.73; N, 12.60.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. customevaporated
  3. customChromatography, with chloroform:methanol (96:4) as the eluent, gave material which
  4. customwas precipitated from dichloromethane and hexane

Sources & evidence

ORD record
ord-5ba40b03e274428b97992edc1d963661
Source dataset
uspto-grants-1995_08
Patent number
US05441960

Reaction notes

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