(2S,3S,4S,5R,6S)-6-{2-[2'-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester → (2S,3S,4S,5R,6S)-6-{2-[2'-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

HRID 1810596Notes

Reaction equation

HRID 1810596 reaction equation
C([O:8][C:9]([C@@H:11]1[C@@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([OH:19])[C@H:13]([O:20][C:21](=[O:55])[CH2:22][C:23]2[CH:24]=[C:25]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=3[CH2:41][N:42]([CH2:53][CH3:54])[C:43]([NH:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:44])[C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[O:12]1)=[O:10])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH2:46]([NH:45][C:43](=[O:44])[N:42]([CH2:41][C:32]1[CH:33]=[C:34]([C:37]([F:40])([F:39])[F:38])[CH:35]=[CH:36][C:31]=1[C:25]1[C:26]([O:29][CH3:30])=[CH:27][CH:28]=[C:23]([CH2:22][C:21]([O:20][C@@H:13]2[O:12][C@H:11]([C:9]([OH:10])=[O:8])[C@@H:16]([OH:17])[C@H:15]([OH:18])[C@H:14]2[OH:19])=[O:55])[CH:24]=1)[CH2:53][CH3:54])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

4

Reactant 1

HCID 66607701(2S,3S,4S,5R,6S)-6-{2-[2'-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

Product 1

HCID 54674328(2S,3S,4S,5R,6S)-6-{2-[2'-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(2S,3S,4S,5R,6S)-6-{2-[2′-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester (0.2 mmol) in EtOAc was treated with 10% palladium on carbon (catalytic) and hydrogenated under a balloon of H2. The solution was filtered over a pad of Celite, and the filtrate was concentrated and purified by preparative HPLC to give the title compound.

Workup

  1. filtrationThe solution was filtered over a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-1fb5f1d8e1b94803a10dc4043f0212d3
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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