Hydrogen Bromide → HCID 86714068, compound

HRID 2206749Notes

Reaction equation

HRID 2206749 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:40]=[CH:39][C:34]4[O:35][CH2:36][CH2:37][O:38][C:33]=4[CH:32]=3)[CH:24]=2)[O:6]1)(=O)C.[BrH:41]>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:40]=[CH:39][C:34]4[O:35][CH2:36][CH2:37][O:38][C:33]=4[CH:32]=3)[CH:24]=2)[O:6][C@H:5]1[Br:41])(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 71110611HCID 71110611, compound

Product 1

HCID 86714068HCID 86714068, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

Compound 137 (100 mg, 0.17 mmol) was treated with 33% HBr in AcOH (350 μL) for 30 min at room temperature. The reaction mixture was diluted with CH2Cl2 (1 mL), stirred for 30 min, diluted with more CH2Cl2 (50 mL), and washed with cold water (10 mL×2), and saturated NaHCO3 solution (40 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (100 mg, 99%) as an off-white solid. The obtained product was used for the next step without purification.

Workup

  1. washwashed with cold water (10 mL×2), and saturated NaHCO3 solution (40 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1728ee45b9444fca4eb6868d2ae1efc
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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