Hydrochloric Acid → HCID 10053779, compound

HRID 732750Notes

Reaction equation

HRID 732750 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]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36])=[CH:31][CH:30]=1)[CH:7]=[CH:6]2.Cl.CCOCC.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[N:21]1([CH2:20][CH2:19][O:18][C:17]2[CH:27]=[CH:28][C:14]([O:13][C:9]3[C:8]([C:29]4[CH:34]=[CH:33][C:32]([S:35]([C:38]([F:39])([F:40])[F:41])(=[O:36])=[O:37])=[CH:31][CH:30]=4)=[CH:7][CH:6]=[C:5]4[C:10]=3[CH:11]=[CH:12][C:3]([OH:2])=[CH:4]4)=[CH:15][CH:16]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 10257749HCID 10257749, compound

Product 1

HCID 10053779HCID 10053779, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve the compound of Example 19 (250 mg, 0.42 mmol) in dichloromethane (5 mL). Add 2M HCl in ether (0.42 mL, 0.84 mmol) and stir for 1 minute. Remove the solvent in vacuo and place on a high vacuum pump for 10 minutes. Dissolve the foam in dry dichloromethane (5 mL), cool to 0° C. and add BBr3 (0.20 mL, 2.1 mmol), dropwise. After 25 minutes, slowly pour into saturated aqueous sodium bicarbonate (10 mL) and extract with dichloromethane (2×10 mL). Dry the combined organic layers with sodium sulfate and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting with methanol (3 to 5%) in dichloromethane with 0.2% ammonium hydroxide to yield 196 mg of the title compound (81%): mass spectrum (ion spray) m/z=572.3 (M+H).

Workup

  1. customRemove the solvent in vacuo and place on a high vacuum pump for 10 minutes
  2. dissolutionDissolve the foam in dry dichloromethane (5 mL)
  3. waitAfter 25 minutes
  4. extractionextract with dichloromethane (2×10 mL)
  5. dry with materialDry the combined organic layers with sodium sulfate
  6. concentrationconcentrate in vacuo
  7. washChromatograph the residue on a SiO2 column eluting with methanol (3 to 5%) in dichloromethane with 0.2% ammonium hydroxide

Sources & evidence

ORD record
ord-27261f8afd784761a1ff4b213dfa8723
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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