Sodium Acetate → HCID 59557721, compound

HRID 1175308Notes

Reaction equation

HRID 1175308 reaction equation
CC([O-])=O.[Na+].C([O:9][CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=2)=[CH:13][C:12]=1[C@H:27]1[C@H:32]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@@H:31]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@H:30]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C@@H:29]([CH2:57][O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[O:28]1)C=C>CC(O)=O.O.Cl[Pd]Cl>[Cl:17][C:15]1[C:14]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][CH:24]=2)=[CH:13][C:12]([C@H:27]2[C@H:32]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C@@H:31]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@H:30]([O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C@@H:29]([CH2:57][O:58][CH2:59][C:60]3[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=3)[O:28]2)=[C:11]([CH2:10][OH:9])[CH:16]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 59557724HCID 59557724, compound

Product 1

HCID 59557721HCID 59557721, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

PdCl2 (23.7 mg, 0.133 mmol, 2.2 eq) and NaOAc (76 mg, 0.285 mmol, 4 eq) were added to a solution of (2S,3S,4R,5R,6R)-2-(2-(allyloxymethyl)-4-chloro-5-(4-ethylbenzyl)phenyl)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran (intermediate O-1) (50 mg, 0.061 mmol) in HOAc:H2O (9:1) (1 mL), and the mixture was stirred at 70° C. for 1 h. Then the mixture was cooled to room temperature, extracted with ethyl acetate, and the combined organic layers were washed with water, dried over anhydrous Na2SO4, concentrated and purified by preparative TLC to obtain 30 mg of intermediate V-1.

Workup

  1. temperatureThen the mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washthe combined organic layers were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. custompurified by preparative TLC

Sources & evidence

ORD record
ord-642c2524643348429325434ab1d1c094
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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