m-Chloroperbenzoic acid → HCID 15952273, compound

HRID 2244249Notes

Reaction equation

HRID 2244249 reaction equation
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:12][CH:11]=1)[CH3:3].C(=O)([O-])[OH:43].[Na+].ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N+:38]([O-:43])[CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:14][CH:15]=1)[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15952866HCID 15952866, compound

Product 1

HCID 15952273HCID 15952273, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10-{[2′-(1-hydroxyethyl)-1,1′-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 52 (0.500 g, 0.92 mmol) in dichloromethane (20 mL) was added saturated aqueous sodium hydrogencarbonate solution (20 mL) followed by 70% 3-chloroperoxybenzoic acid (909 mg, 3.69 mmol) and the biphasic mixture was stirred vigorously for 1 hour. The reaction was quenched by the addition of 5% aqueous sodium metabisulfite solution (20 mL), the mixture stirred vigorously for 5 minutes, then partitioned between ethyl acetate (100 mL) and 2 M sodium hydroxide (100 mL). The organic layer was separated, washed with 2 M sodium hydroxide (2×100 mL), water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a white solid. Purification by flash chromatography using a solvent gradient of 3 to 10% methanol in dichloromethane gave the title compound (31.1 mg, 6%) as a white solid, m.p. 213-215° C.

Workup

  1. customThe reaction was quenched by the addition of 5% aqueous sodium metabisulfite solution (20 mL)
  2. stirringthe mixture stirred vigorously for 5 minutes
  3. custompartitioned between ethyl acetate (100 mL) and 2 M sodium hydroxide (100 mL)
  4. customThe organic layer was separated
  5. washwashed with 2 M sodium hydroxide (2×100 mL), water (100 mL) and brine (100 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a white solid
  9. customPurification by flash chromatography

Sources & evidence

ORD record
ord-88c2d5b68de04c84b8a164f1d27f27aa
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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