Hydrochloric Acid → HCID 18533202, compound

HRID 413430Notes

Reaction equation

HRID 413430 reaction equation
C([O:5][C:6]1[CH:7]=[C:8]([CH:38]=[CH:39][CH:40]=1)[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:31]S(C(C)(C)C)=O)([C:22]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([F:30])[CH:23]=1)[C:16]1[N:17]([CH3:21])[CH:18]=[N:19][CH:20]=1)(C)(C)C.Cl>CO.O1CCOCC1>[NH2:31][C:15]([C:22]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([F:30])[CH:23]=1)([C:16]1[N:17]([CH3:21])[CH:18]=[N:19][CH:20]=1)[CH2:14][CH2:13][CH2:12][CH2:11][O:10][CH2:9][C:8]1[CH:38]=[CH:39][CH:40]=[C:6]([OH:5])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86758981HCID 86758981, compound

Product 1

HCID 18533202HCID 18533202, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Methyl-propane-2-sulfinic acid [5-(3-tert-butoxy-benzyloxy)-1-(4-cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-pentyl]-amide (A) (0.396 g, 0.58 mmol) was dissolved in methanol (15 mL) and treated with 4M HCl in dioxane (9 mL). After 1 h, the reaction mixture was concentrated in vacuo, azeotroped with CH2Cl2 (3×), rinsed with CH2Cl2, and the solid collected to give enantiomer A of the title compound. MS (M+1) 409. Using the same procedure, diastereomer B (Step D) (0.110 g, 0.161 mmol) gave enantiomer B of the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customazeotroped with CH2Cl2 (3×)
  3. washrinsed with CH2Cl2
  4. customthe solid collected

Sources & evidence

ORD record
ord-051f30c3919f40b29b4a5cf3ba2ca87a
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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