Hydrochloric Acid → HCID 68519548, compound

HRID 732777Notes

Reaction equation

HRID 732777 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-3c582b25f726453b9426b58379ef2c2c
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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