m-Chloroperbenzoic acid → HCID 86726799, compound

HRID 1499574Notes

Reaction equation

HRID 1499574 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[OH:12][C:13]1([CH3:40])[C@@H:18]([CH3:19])[CH2:17][N:16]([C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]3[CH2:29][CH2:30][CH2:31][C:21]=23)[CH2:15][C@H:14]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36]>C(Cl)Cl>[OH:12][C:13]1([CH3:40])[C@@H:18]([CH3:19])[CH2:17][N:16]([C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N+:23]([O-:9])=[C:22]3[CH2:29][CH2:30][CH2:31][C:21]=23)[CH2:15][C@H:14]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 86726797HCID 86726797, compound

Product 1

HCID 86726799HCID 86726799, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (260 mg, 1.5 mmol) was added to a mixture of tert-butyl [(3R,5S)-4-hydroxy-4,5-dimethyl-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate (312 mg, 0.768 mmol) in DCM (3.2 mL). After 2 h, LCMS showed only 30% conversion of starting material. mCPBA was added several more times (to a total amount of about 10 eq.) until LCMS showed complete consumption of starting material (after approximately 7 h). A saturated solution of NaHCO3 was then added to the mixture and the resulting mixture was extracted with DCM. The combined organic extracts were dried and then concentrated to dryness under reduced pressure. The crude sub-title compound was used in the next step without further purification. LCMS calc. for C20H31N4O6 (M+H)+ m/z=423.2. found 423.2.

Workup

  1. customconsumption of starting material (after approximately 7 h)
  2. additionA saturated solution of NaHCO3 was then added to the mixture
  3. extractionthe resulting mixture was extracted with DCM
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe crude sub-title compound was used in the next step without further purification

Sources & evidence

ORD record
ord-ee9ca98d855c4e9a905c815e3c7cf56a
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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