m-Chloroperbenzoic acid → HCID 68195077, compound

HRID 2370639Notes

Reaction equation

HRID 2370639 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:19](=O)[C:18]2[C:13](=[N:14][C:15](SC)=[N:16][CH:17]=2)[N:12]2[CH:23]=[CH:24][N:25]=[C:11]12.ClC1C=C(C=CC=1)C(OO)=[O:31].[NH2:37][C:38]1[CH:47]=[C:46]2[C:41]([C:42]3([CH2:56][CH2:55]3)[CH2:43][N:44]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:45]2)=[CH:40][CH:39]=1>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:19]2[N:14]=[CH:15][N:16]=[CH:17][C:18]=2[C:13]2=[N:25][C:24]([NH:37][C:38]3[CH:47]=[C:46]4[C:41]([C:42]5([CH2:55][CH2:56]5)[CH2:43][N:44]([C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])[CH2:45]4)=[CH:40][CH:39]=3)=[CH:23][N:12]2[C:11]1=[O:31]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 68194310HCID 68194310, compoundHCID 68195399HCID 68195399, compound

Product 1

HCID 68195077HCID 68195077, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 123A (600.0 mg, 1.514 mmol) and m-chloroperoxybenzoic acid (407 mg, 1.817 mmol) in CH2Cl2 (14 ml) was stirred for 20 minutes. tert-Butyl 7′-amino-1′H-spiro[cyclopropane-1,4′-isoquinoline]-2′(3′H)-carboxylate (499 mg, 1.817 mmol) was added to the reaction mixture. After 25 minutes, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous NaHCO3, and brine. The organic layer was dried over MgSO4, filtered, concentrated, and purified on a 40 g column using the ISCO Companion flash system eluting with hexane/ethyl acetate (6:4 to 4:6) to provide the title compound.

Workup

  1. washwashed with saturated aqueous NaHCO3, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on a 40 g column
  6. washeluting with hexane/ethyl acetate (6:4 to 4:6)

Sources & evidence

ORD record
ord-fafaf62e01374768b4fa784270fe8440
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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