Hydrochloric Acid → HCID 58361511, compound

HRID 2076454Notes

Reaction equation

HRID 2076454 reaction equation
[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]([OH:26])[CH2:23][CH:24]=O)=[N:18]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][NH2:28].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].Cl.C([O-])(O)=O.[Na+]>CO.CC(O)=O>[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]([OH:26])[CH2:23][CH2:24][NH:28][CH3:27])=[N:18]3)=[CH:13][CH:12]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58361501HCID 58361501, compound

Product 1

HCID 58361511HCID 58361511, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound 18 (190 mg, 0.435 mmol) in MeOH (1 mL) were added methyl amine (0.04 mL, 0.462 mmol), HOAc (0.005 mL), and NaBH(OAc)3 (200 mg, 0.943 mmol). The reaction was stirred at 25° C. for 20 h. After the reaction was complete, 1 N HCl (0.1 mL) was added to the reaction mixture and then neutralized with saturated aq. NaHCO3. The resulting mixture was extracted with EtOAc, and the organic layers were pooled, washed with brine, and dried over Na2SO4. Solvent was removed in vacuo to afford 19 (160 mg, 0.355 mmol, 81%) as a colorless oil, which was used without further purification. MS-ESI (m/z): [M+H]+ calculated for C19H20BrN2O4S, 451.03 (79Br) and 453.03 (81Br); found 450.89 (79Br) and 453.01 (81Br).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-9f7887113da34546ad01625c8ef0307d
Source dataset
uspto-grants-2011_04
Patent number
US07923562B2

Reaction notes

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