m-Chloroperbenzoic acid → HCID 67435137, compound

HRID 245576Notes

Reaction equation

HRID 245576 reaction equation
[F:1][C:2]1[C:3]2[O:28][N:27]=[C:26]([S:29][CH3:30])[C:4]=2[CH:5]=[C:6]2[C:19]=1[N:18]1[CH2:20][C@@H:21]([CH3:25])[O:22][C@@H:23]([CH3:24])[C@@H:17]1[C:8]1([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:9]1=[O:16])[CH2:7]2.ClC1C=CC=C(C(OO)=[O:39])C=1>C(Cl)Cl>[F:1][C:2]1[C:3]2[O:28][N:27]=[C:26]([S:29]([CH3:30])=[O:39])[C:4]=2[CH:5]=[C:6]2[C:19]=1[N:18]1[CH2:20][C@@H:21]([CH3:25])[O:22][C@@H:23]([CH3:24])[C@@H:17]1[C:8]1([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:9]1=[O:16])[CH2:7]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67433632HCID 67433632, compound

Product 1

HCID 67435137HCID 67435137, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2R,4S,4aS)-rel-11-fluoro-2,4-dimethyl-8-(methylsulfanyl)-1,2,4,4a-tetrahydro-2′H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5′-pyrimidine]-2′,4′,6′(1′H,3′H)-trione Example 62, 50 mg, 0.11 mmol) in dry DCM (1 mL) was added m-chloroperbenzoic acid (39 mg, 0.23 mmol) and stirred at room temperature for 1 hours. Solvents were evaporated and the residue thus obtained purified over a silica gel column to give product as solid. Yield: 18 mg (35%).

Workup

  1. customSolvents were evaporated
  2. customthe residue thus obtained
  3. custompurified over a silica gel column
  4. customto give product as solid

Sources & evidence

ORD record
ord-e429a60ff79749fabb1b06824d87abcd
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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