Hydrochloric Acid → HCID 66848355, compound

HRID 475435Notes

Reaction equation

HRID 475435 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C@@H:15]([NH:23][S@](C(C)(C)C)=O)[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:7][O:8][C:4]=2[CH:3]=1.Cl>ClCCl.CO>[Br:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C@@H:15]([NH2:23])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71224308HCID 71224308, compound2×

Product 1

HCID 66848355HCID 66848355, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)—N-((1S)-1-(2-(6-bromobenzo[d]isoxazol-3-yl)phenyl)-2-(pyridin-2-yl)ethyl)-2-methylpropane-2-sulfinamide (Compound 14a) (1.76 g) dissolved in dichloromethane (10 mL) was added 2N hydrochloric acid (10 mL) and the mixture left to stand at room temperature. The resulting mixture was taken up in methanol and loaded onto a 20 g SCX column and eluted with neat methanol, followed by ammonia-methanol and the fractions containing product were evaporated to give the title product (1.25 g) as a clear yellow oil.

Workup

  1. waitthe mixture left
  2. customto stand at room temperature
  3. washeluted with neat methanol
  4. additionthe fractions containing product
  5. customwere evaporated

Sources & evidence

ORD record
ord-a3d32b93bc7a4c74aa1b5c4bc400f359
Source dataset
uspto-grants-2014_01
Patent number
US08637551B2

Reaction notes

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