HCID 86714099, compound → HCID 86714098, compound

HRID 576437Notes

Reaction equation

HRID 576437 reaction equation
Br[C:2]1[C:15]([CH:16]2[C@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:20]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:19]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:18]([CH2:46][O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[O:17]2)=[CH:14][C:13]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([O:62][CH2:63][CH3:64])=[CH:58][CH:57]=2)=[C:12]([Cl:65])[C:3]=1[O:4][CH2:5][C:6](N(OC)C)=[O:7].[Li]CCCC>C1COCC1.[NH4+].[Cl-]>[Cl:65][C:12]1[C:3]2[O:4][CH2:5][C:6](=[O:7])[C:2]=2[C:15]([CH:16]2[C@H:21]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@@H:20]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@H:19]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C@@H:18]([CH2:46][O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[O:17]2)=[CH:14][C:13]=1[CH2:55][C:56]1[CH:57]=[CH:58][C:59]([O:62][CH2:63][CH3:64])=[CH:60][CH:61]=1

Participants

5

Reactant 2

HCID 86714099HCID 86714099, compoundHCID 178418339Butyllithium

Product 1

HCID 86714098HCID 86714098, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 2-(2-bromo-6-chloro-5-(4-ethoxybenzyl)-3-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenoxy)-N-methoxy-N-methylacetamide (1.02 g, 1.06 mmole) in THF (15 mL) was added nBuLi (1.3 mL, 3.18 mmole, 2.5M in hexane) at −78° C. The resulting solution was warmed up to rt and stirred overnight, diluted with a saturated NH4Cl and extracted with ethyl acetate. The organic layer was washed with water then brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the title compound (429 mg, 49%) as a yellow gum.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on Biotage® purification apparatus

Sources & evidence

ORD record
ord-f256f021b46441f99b414c7b71607c06
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

Loading…