Hydrochloric Acid → HCID 68517827, compound

HRID 748896Notes

Reaction equation

HRID 748896 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22]C)[CH:18]=3)[C:13]=2[O:24][C:25]2[CH:39]=[CH:38][C:28]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][CH:26]=2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].Cl.B(Br)(Br)Br.O>C(OCC)(=O)C.C(OCC)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13]([O:24][C:25]3[CH:39]=[CH:38][C:28]([O:29][CH2:30][CH2:31][N:32]4[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]4)=[CH:27][CH:26]=3)=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15]3)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 25134Boron tribromideHCID 59751448HCID 59751448, compound

Product 1

HCID 68517827HCID 68517827, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve the product of Example 28 in ethyl acetate (10 mL) and diethyl ether (5 mL). Add 2M HCl in diethyl ether (0.6 mL, 1.2 mmol). Concentrate the slurry and dry in vacuo. Dilute the residue in dichloromethane (5.0 mL) and blanket with nitrogen. Cool the solution to 0° C. with external ice bath. Add BBr3 (0.1 mL, 1.1 mmol). After 1 hour, add water (1.0 mL) and dichloromethane (10 mL). Separate the layers, wash the organic layer with saturated aqueous NaHCO3 (10 mL), brine (10 mL), dry with MgSO4, filter, and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting with a step gradient of methanol/dichloromethane (0 to 5%) to give 120 mg of the title compound (68%): mass spectrum (ion spray): m/z=552.2 (M+H).

Workup

  1. concentrationConcentrate the slurry
  2. customdry in vacuo
  3. additionDilute the residue in dichloromethane (5.0 mL)
  4. customSeparate the layers
  5. washwash the organic layer with saturated aqueous NaHCO3 (10 mL), brine (10 mL)
  6. dry with materialdry with MgSO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. washChromatograph the residue on a SiO2 column eluting with a step gradient of methanol/dichloromethane (0 to 5%)

Sources & evidence

ORD record
ord-9e82d0dc6e4641d590610abcf97e747d
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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