Methyl morpholine oxide → (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

HRID 563837Notes

Reaction equation

HRID 563837 reaction equation
[CH2:1]([NH:8][C:9](=[O:36])[N:10]([CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[C:24]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[C:26]([CH2:32][C:33]([OH:35])=[O:34])[CH:25]=1)[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37]([O:44][C:45]([C@@H:47]1[C@@H:52]([OH:53])[C@H:51]([OH:54])[C@@H:50]([OH:55])[C@H:49](O)[O:48]1)=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N+]1([O-])CCOCC1>CC#N>[CH2:37]([O:44][C:45]([C@@H:47]1[C@@H:52]([OH:53])[C@H:51]([OH:54])[C@@H:50]([OH:55])[C@H:49]([O:34][C:33](=[O:35])[CH2:32][C:26]2[CH:25]=[C:24]([C:15]3[CH:16]=[CH:17][C:18]([C:20]([F:22])([F:23])[F:21])=[CH:19][C:14]=3[CH2:13][N:10]([CH2:11][CH3:12])[C:9]([NH:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:36])[C:29]([O:30][CH3:31])=[CH:28][CH:27]=2)[O:48]1)=[O:46])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 82029Methyl morpholine oxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44158492Am-211HCID 58148857(2S,3S,4S,5R,6R)-benzyl 3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate

Product 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[2′-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid (0.110 g, 0.2 mmol), (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester (0.060 g, 0.2 mmol), HATU (0.026 g, 0.2 mmol), and N-methylmorpholine-N-oxide (0.05 mL, 0.4 mmol) were combined in MeCN (2 mL) and stirred for 2 days at room temperature. The mixture was concentrated, and the residue was purified by preparative HPLC to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3b59b7eadfad4c0fb3f27b75652f6e6e
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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