Hydrogen Bromide → HCID 66885751, compound

HRID 2204043Notes

Reaction equation

HRID 2204043 reaction equation
C(O[CH:5]1[C@@H:10]([O:11][C:12](=[O:14])[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][CH2:38][CH3:39])=[CH:33][CH:32]=3)[CH:24]=2)[O:6]1)(=O)C.[BrH:40]>CC(O)=O.C(Cl)Cl>[C:16]([O:15][C@@H:9]1[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]([O:37][CH2:38][CH3:39])=[CH:35][CH:36]=3)[CH:24]=2)[O:6][C@@H:5]([Br:40])[C@H:10]1[O:11][C:12](=[O:14])[CH3:13])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 57558243HCID 57558243, compound

Product 1

HCID 66885751HCID 66885751, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

The tetraacetate of step A (8.08 g, 14.4 mmol) was treated with 33% HBr in AcOH (30 ml) for 1 hour. The reaction was diluted with CH2Cl2 (60 ml), stirred for 30 minutes, diluted with more DCM, washed 3× with ice cold H2O and with sat. aq. NaHCO3 (with back extraction), dried over MgSO4, filtered, and concentrated under vacuum to give acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-2-bromo-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-tetrahydro-pyran-3-yl ester.

Workup

  1. washwashed 3× with ice cold H2O
  2. dry with materialwith sat. aq. NaHCO3 (with back extraction), dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4a267df03a264950a13d6e86b183441e
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

Loading…