Hydrochloric Acid → HCID 66661852, compound

HRID 2275637Notes

Reaction equation

HRID 2275637 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:13]([C:15]2([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH2:17][CH2:16]2)=[O:14])[CH2:9]1)(C)(C)C.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:7][C@H:8]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[CH2:16][CH2:17]3)=[O:14])[CH2:9]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-255e9864ada5480681993c2c21141426
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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