Hydrogen Bromide → HCID 178476345, compound

HRID 991142Notes

Reaction equation

HRID 991142 reaction equation
[CH3:1][C:2]1([CH3:36])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[C@@H:19]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[O:18][C@@H:13]2OC(=O)C)[CH3:10])[C:4](=[O:35])[CH2:3]1.[BrH:37]>C(O)(=O)C.C(Cl)Cl>[CH3:1][C:2]1([CH3:36])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[C@@H:19]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[O:18][C@@H:13]2[Br:37])[CH3:10])[C:4](=[O:35])[CH2:3]1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 178476369HCID 178476369, compound

Product 1

HCID 178476345HCID 178476345, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethylamino]-1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (100 mg, 0.19 mmol) and HBr in acetic acid (45%) (1.0 ml) was stirred at room temperature for 30 min. The reaction mixture was diluted with cold CH2Cl2 (10 ml), washed twice with cold H2O (30 ml), saturated NaHCO3 solution (20 ml) and with H2O again (20 ml). The organic phase was dried over MgSO4 and evaporated, giving 2-Deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide (3) (95 mg, 91%).

Workup

  1. washwashed twice with cold H2O (30 ml), saturated NaHCO3 solution (20 ml) and with H2O again (20 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-876e5781af474763b00d5505fdc37de6
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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