HCID 86761745, compound → HCID 86761744, compound

HRID 1805937Notes

Reaction equation

HRID 1805937 reaction equation
[C:1](=[O:64])([O:51][CH:52]1[CH2:57][O:56]C(C2C=CC=CC=2)[O:54][CH2:53]1)[O:2][C@H:3]([C:37]1[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[C:39]([C:47]([F:50])([F:49])[F:48])[CH:38]=1)[C@@H:4]([N:6]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[C:22]([CH:24]([CH3:26])[CH3:25])[C:21]([F:27])=[CH:20][C:19]=1[O:28][CH3:29])[CH3:5]>[Pd].CCOC(C)=O>[C:1](=[O:64])([O:51][CH:52]([CH2:57][OH:56])[CH2:53][OH:54])[O:2][C@H:3]([C:37]1[CH:38]=[C:39]([C:47]([F:49])([F:48])[F:50])[CH:40]=[C:41]([C:43]([F:45])([F:46])[F:44])[CH:42]=1)[C@@H:4]([N:6]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:7][C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[C:22]([CH:24]([CH3:25])[CH3:26])[C:21]([F:27])=[CH:20][C:19]=1[O:28][CH3:29])[CH3:5]

Participants

4

Reactant 1

HCID 86761745HCID 86761745, compound

Product 1

HCID 86761744HCID 86761744, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 10% palladium on carbon (9.13 mg, 8.57 μmol) in a solution of (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-phenyl-1,3-dioxan-5-yl carbonate (78.7 mg, 0.086 mmol) in EtOAc (6.60 mL) was stirred under H2 (double balloon pressure) at 25° C. for 15 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-hydroxy-1-(hydroxymethyl)ethyl carbonate. LCMS calc.=852.26; found=852.10 (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-12bd51f5e8fd4a78a0a0dbd20c6b6f6a
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

Loading…