HCID 86657399, compound → HCID 86657398, compound

HRID 1805933Notes

Reaction equation

HRID 1805933 reaction equation
[C:1](=[O:81])([O:32][C@H:33]([C:67]1[CH:72]=[C:71]([C:73]([F:76])([F:75])[F:74])[CH:70]=[C:69]([C:77]([F:80])([F:79])[F:78])[CH:68]=1)[C@@H:34]([N:36]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:37][C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[CH:40][C:39]=1[C:48]1[CH:53]=[C:52]([CH:54]([CH3:56])[CH3:55])[C:51]([F:57])=[CH:50][C:49]=1[O:58][CH3:59])[CH3:35])[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][P:12]([O:22]CC2C=CC=CC=2)([O:14]CC2C=CC=CC=2)=[O:13])=[CH:5][C:4]=1[O:30][CH3:31]>[Pd].C(O)C>[C:1](=[O:81])([O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][P:12]([OH:14])([OH:22])=[O:13])=[CH:5][C:4]=1[O:30][CH3:31])[O:32][C@H:33]([C:67]1[CH:72]=[C:71]([C:73]([F:76])([F:75])[F:74])[CH:70]=[C:69]([C:77]([F:78])([F:79])[F:80])[CH:68]=1)[C@@H:34]([N:36]([C:60]([O:62][C:63]([CH3:64])([CH3:65])[CH3:66])=[O:61])[CH2:37][C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[CH:40][C:39]=1[C:48]1[CH:53]=[C:52]([CH:54]([CH3:55])[CH3:56])[C:51]([F:57])=[CH:50][C:49]=1[O:58][CH3:59])[CH3:35]

Participants

4

Reactant 1

HCID 86657399HCID 86657399, compound

Product 1

HCID 86657398HCID 86657398, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 10% palladium on carbon (7.9 mg, 0.074 mmol) in a solution of 4-(2-{[bis(benzyloxy)phosphoryl]oxy}ethyl)-2-methoxyphenyl (1R ,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-((tert-butoxycarbonyl){[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}amino)propyl carbonate (86.2 mg, 0.074 mmol) in ethanol (5.7 mL) was stirred under H2 (double balloon pressure) at 25° C. for 5 h. The reaction mixture was filtered through a plug of Celite and the filtrate was concentrated in vacuo to afford (1R,2S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-((tert-butoxycarbonyl){[4′-fluoro-5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}amino)propyl 2-methoxy-4-[2-(phosphonooxy)ethyl]phenyl carbonate. LCMS calc.=1008.8; found=1008.8 (M+Na)+.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6478893f2ad9442e8991167b1678a3bf
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

Loading…