Hydrogen Bromide → HCID 86729310, compound

HRID 1474610Notes

Reaction equation

HRID 1474610 reaction equation
C(O[CH:5]1[C@@H:10]([O:11][C:12](=O)[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([O:19][C:20](=[O:22])[CH3:21])[C@H:7]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37]C(=O)C)=[CH:33][CH:32]=3)[CH:24]=2)[O:6]1)(=O)C.[BrH:41].[OH2:42]>CC(O)=O.C(Cl)Cl>[C:12]([O:11][C@H:10]1[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([O:19][C:20](=[O:22])[CH3:21])[C@H:7]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([OH:37])=[CH:35][CH:36]=3)[CH:24]=2)[O:6][CH:5]1[Br:41])(=[O:42])[CH3:13]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 86729311HCID 86729311, compound

Product 1

HCID 86729310HCID 86729310, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To (3S,4R,5S,6S)-6-(3-(4-acetoxybenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (2.03 g, 4.03 mmol) a 33% solution of HBr in AcOH (6 mL) was added at r.t. and stirred for 0.1 h. The reaction mixture was diluted with DCM (20 mL) and stirred for 30 min. Water was added to the resulting mixture and stirred for another 1 h. It was diluted with DCM (50 mL), washed with water (50 mL), saturated NaHCO3 solution (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo to afford the title compound (2.02 g, 90%)

Workup

  1. stirringstirred for 30 min
  2. stirringstirred for another 1 h
  3. washwashed with water (50 mL), saturated NaHCO3 solution (50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-1f1624bd0e6a4e5699d8565a8733d851
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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