HCID 87557856, compound → HCID 59557700, compound

HRID 1175313Notes

Reaction equation

HRID 1175313 reaction equation
CS([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=2)=[CH:10][C:9]=1[C@H:24]1[C@H:29]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:28]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:27]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:26]([CH2:54][O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[O:25]1)(=O)=O.[C:63]([CH2:67]O[Na])([F:66])([F:65])[F:64]>C(CO)(F)(F)F>[CH2:47]([O:46][C@H:27]1[C@H:28]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@@H:29]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@H:24]([C:9]2[CH:10]=[C:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=3)[C:12]([Cl:14])=[CH:13][C:8]=2[CH2:7][CH2:6][O:5][CH2:67][C:63]([F:66])([F:65])[F:64])[O:25][C@@H:26]1[CH2:54][O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

4

Reactant 2

HCID 87557856HCID 87557856, compoundHCID 178506350HCID 178506350, compound2×

Product 1

HCID 59557700HCID 59557700, compound

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent2×

Procedure

The solution of 5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenethyl methanesulfonate (58 mg, 0.066 mmol) in 0.8 mL of 1.5 M CF3CH2ONa in CF3CH2OH was stirred at 60° C. under argon. After it was stirred for about 9 h, an additional 0.6 mL of 1.5 M of CF3CH2ONa in CF3CH2OH was added and the mixture was stirred for another 15 h at 60° C. After removal of the volatiles with a rotary evaporator under vacuum, the residue was partitioned between water and EtOAC. The organic layer was separated, washed with brine and dried over Na2SO4. Concentration gave the crude product, which was purified by preparative TLC to yield 30 mg of title compound. MS ESI (m/z) 896 (M+NH4)+, calc. 878.

Workup

  1. stirringthe mixture was stirred for another 15 h at 60° C
  2. customAfter removal of the volatiles
  3. customwith a rotary evaporator under vacuum
  4. customthe residue was partitioned between water and EtOAC
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationConcentration
  9. customgave the crude product, which
  10. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-674b9a1edf364cbd8b11140abf1d45f3
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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