Methanol → N-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzyl)-N-cyclopropylacetamide

HRID 2403726Notes

Reaction equation

HRID 2403726 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:20]([C@H:23]2[C@H:28]([O:29]CC3C=CC=CC=3)[C@@H:27]([O:37]CC3C=CC=CC=3)[C@H:26]([O:45]CC3C=CC=CC=3)[C@@H:25]([CH2:53][O:54]CC3C=CC=CC=3)[O:24]2)=[CH:19][C:3]=1[CH2:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][N:10]([CH:14]2[CH2:16][CH2:15]2)[C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1.CO.ClC1C=CC=CC=1Cl>C1COCC1.[Pd]>[Cl:1][C:2]1[CH:22]=[CH:21][C:20]([C@H:23]2[C@H:28]([OH:29])[C@@H:27]([OH:37])[C@H:26]([OH:45])[C@@H:25]([CH2:53][OH:54])[O:24]2)=[CH:19][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH:14]2[CH2:15][CH2:16]2)[C:11](=[O:13])[CH3:12])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 72391,2-DichlorobenzeneHCID 57684697HCID 57684697, compound

Product 1

HCID 56666658N-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzyl)-N-cyclopropylacetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzyl)-N-cyclopropylacetamide (intermediate AR) (20 mg) in THF:CH3OH (v/v=1:1) (4 mL) at room temperature was added Pd/C and 1,2-dichlorbenzene (0.05 mL). The mixture was stirred under H2. After LC-MS showed the starting material was consumed, Pd/C was removed by filtration, and the solvent was removed under reduced pressure. The crude product was purified by preparative LC-MS to give compound AS (4 mg). 1H NMR (400 Hz, CD3OD): δ 0.77-0.87 (4H, m), 2.26 (3H, s), 2.62-2.66 (1H, m), 3.26 (1H, d, J=8.8 Hz), 3.36-3.46 (3H, m), 3.66-3.69 (1H, m), 3.86 (1H, d, J=12.8 Hz), 4.02-4.12 (3H, m), 4.56 (2H, s), 7.11-7.16 (4H, m), 7.26-7.29 (1H, m), 7.33-7.35 (2H, m); MS ESI (m/z): 520 (M+HCO2)−.

Workup

  1. customwas consumed
  2. customPd/C was removed by filtration
  3. customthe solvent was removed under reduced pressure
  4. customThe crude product was purified by preparative LC-MS
  5. customto give compound AS (4 mg)

Sources & evidence

ORD record
ord-3a297ee82adc48739b3608b6ca442da9
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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