Hydrochloric Acid → HCID 68519548, compound

HRID 748912Notes

Reaction equation

HRID 748912 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:16][CH:15]=1)=[C:8]([C:29]1[CH:34]=[CH:33][C:32]([S:35][CH3:36])=[C:31]([CH3:37])[CH:30]=1)[CH:7]=[CH:6]2.Cl.B(Br)(Br)Br.O>C(OCC)(=O)C.C(OCC)C>[CH3:37][C:31]1[CH:30]=[C:29]([C:8]2[C:9]([O:13][C:14]3[CH:28]=[CH:27][C:17]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]3)[CH:34]=[CH:33][C:32]=1[S:35][CH3:36]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 25134Boron tribromideHCID 59751442HCID 59751442, compound

Product 1

HCID 68519548HCID 68519548, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve the product of Example 47 in ethyl acetate (10 mL) and diethyl ether (5 mL). Add 2M HCl in diethyl ether (5 mL, 10.0 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 and add BBr3 (0.3 mL, 3.2 mmol). After 1 hour, add water (1.0 mL) and ethyl acetate (10 mL). Separate the layers, wash the organic layer with saturated aqueous NaHCO3 (10 mL) and brine (10 mL). Dry with MgSO4, filter, and concentrate in vacuo. Chromatograph the residue on a column eluting the material with a step gradient of methanol in dichloromethane (0 to 0.5%) to give 330 mg of the title compound (92%): mass spectrum (ion spray): m/z=500.3 (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) and brine (10 mL)
  6. dry with materialDry with MgSO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. washChromatograph the residue on a column eluting the material with a step gradient of methanol in dichloromethane (0 to 0.5%)

Sources & evidence

ORD record
ord-fe1109b0e8954c54bf1e7035dc481acd
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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