m-Chloroperbenzoic acid → HCID 67346398, compound

HRID 237257Notes

Reaction equation

HRID 237257 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2C=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:31])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[OH:31])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 87086903HCID 87086903, compound

Product 1

HCID 67346398HCID 67346398, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a CH2Cl2 (25 mL) solution of the title compound of Step A (1.4 g, 4.3 mmol) was added 77% m-CPBA (1.4 g, 6.2 mmol). After 18 h, additional CH2Cl2 was added and the reaction washed with saturated NaHCO3 (aq.) and 10% Na2S2O5 until KI paper negative. The combined organic layers were dried then treated with MeOH (25 mL) and 1N NaOH (25 mL). After 15 h, the reaction was acidified with 1M KHSO4 then extracted with EtOAc (2×). The combined organic layers were washed with brine and dried to give the title compound as a white solid. 1H NMR (CDCl3): 6.96 (s, 1H), 6.82-6.80 (m, 1H), 6.73 (d, J=8.6 Hz, 1H), 5.62 (s, 1H), 4.91 (s, 1H), 3.66-3.46 (m, 4H), 2.20-2.11 (m, 2H), 1.47 (s, 9H).

Workup

  1. washthe reaction washed with saturated NaHCO3 (aq.) and 10% Na2S2O5 until KI paper negative
  2. customThe combined organic layers were dried
  3. additionthen treated with MeOH (25 mL) and 1N NaOH (25 mL)
  4. waitAfter 15 h
  5. extractionthen extracted with EtOAc (2×)
  6. washThe combined organic layers were washed with brine
  7. customdried

Sources & evidence

ORD record
ord-9837502c913340699380870af8ddc24d
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

Loading…