Hydrochloric Acid → HCID 66661852, compound

HRID 969188Notes

Reaction equation

HRID 969188 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][C@H:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.C(#N)C.C(N(CC)C(C)C)(C)C.[Cl:39][C:40]1[C:41]([CH3:50])=[C:42]([S:46](Cl)(=[O:48])=[O:47])[CH:43]=[CH:44][CH:45]=1.C(O)(C(F)(F)F)=O>O1CCOCC1.CO>[Cl:39][C:40]1[C:41]([CH3:50])=[C:42]([S:46]([NH:18][C@H:15]2[CH2:16][CH2:17][N:13]([C:11]([C:8]3([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[CH2:9][CH2:10]3)=[O:12])[CH2:14]2)(=[O:48])=[O:47])[CH:43]=[CH:44][CH:45]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 68463134HCID 68463134, compound

Product 1

HCID 66661852HCID 66661852, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl ((3S)-1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-yl)carbamate (7.30 mg, 0.0000200 mol) was treated with hydrogen chloride in 1,4-dioxane (4.0 M, 0.50 mL) at rt for 30 minutes. The solvent was evaporated under reduced pressure and acetonitrile (1.0 mL, 0.019 mol) was added. The mixture was then treated with N,N-diisopropylethylamine (20.0 μL, 0.000115 mol), followed by the addition of 3-chloro-2-methylbenzenesulfonyl chloride (4.50 mg, 0.0000200 mol) at rt. The reaction mixture was stirred at rt for 1 h and then acidified (pH=2.0) with TFA. The solution was diluted with methanol (0.80 mL) and was submitted for purification by prep-HPLC to give the desired product. LCMS: m/z 454.1 (M+H)+

Workup

  1. additionwas added
  2. customwas submitted for purification by prep-HPLC

Sources & evidence

ORD record
ord-f51673ee739f49db908b8ad7bbcd7dd7
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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