Hydrochloric Acid → HCID 68518351, compound

HRID 748906Notes

Reaction equation

HRID 748906 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]([CH2:38][C:39]([F:42])([F:41])[F:40])(=[O:37])=[O:36])=[CH:31][CH:30]=1)[CH:7]=[CH:6]2.Cl.C(OCC)C.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]([CH2:38][C:39]([F:40])([F:41])[F:42])(=[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 59751452HCID 59751452, compound

Product 1

HCID 68518351HCID 68518351, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve the compound of Example 37 (26 mg, 0.043 mmol) in dichloromethane (1 mL) and add 2M HCl in diethyl ether (43 μL, 0.086 mmol). Remove the solvents in vacuo and place on a high vacuum pump for 10 minutes. Dissolve the resultant foam in dry dichloromethane (1 mL) and cool to 0° C. Add BBr3 (20 μL, 0.22 mmol) dropwise and stir at 0° C. for 1 hour. Pour the reaction into cold saturated aqueous sodium bicarbonate (5 mL) and extract with dichloromethane (2×5 mL). Dry the combined organic phases with sodium sulfate, filter, and concentrate in vacuo. Purify the resultant oil on a SiO2 column with methanol in dichloro methane (0 to 8%) to yield 16 mg of the title compound (64%): mass spectrum (ion spray) m/z=586.4 (M+H).

Workup

  1. customRemove the solvents in vacuo and place on a high vacuum pump for 10 minutes
  2. dissolutionDissolve the resultant foam in dry dichloromethane (1 mL)
  3. additionPour
  4. extractionextract with dichloromethane (2×5 mL)
  5. dry with materialDry the combined organic phases with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the resultant oil on a SiO2 column with methanol in dichloro methane (0 to 8%)

Sources & evidence

ORD record
ord-6381dac1a7654674811339179f0de525
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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