m-Chloroperbenzoic acid → HCID 71593638, compound

HRID 2405505Notes

Reaction equation

HRID 2405505 reaction equation
[CH3:1][N:2]([CH3:47])[CH2:3][CH2:4][NH:5][C:6]([C@:8]12[CH2:43][CH2:42][C@@H:41]([CH:44]([CH3:46])[CH3:45])[C@@H:9]1[C@@H:10]1[C@@:23]([CH3:26])([CH2:24][CH2:25]2)[C@@:22]2([CH3:27])[C@@H:13]([C@:14]3([CH3:40])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7].ClC1C=C(C=CC=1)C(OO)=[O:53]>C(Cl)Cl>[C:34]([C:33]1[CH:38]=[CH:39][C:30]([C:17]2[C:18]([CH3:29])([CH3:28])[C@H:19]3[C@:14]([CH3:40])([CH2:15][CH:16]=2)[C@@H:13]2[C@:22]([CH3:27])([C@@:23]4([CH3:26])[C@H:10]([CH2:11][CH2:12]2)[C@H:9]2[C@H:41]([CH:44]([CH3:46])[CH3:45])[CH2:42][CH2:43][C@:8]2([C:6]([NH:5][CH2:4][CH2:3][N+:2]([O-:53])([CH3:1])[CH3:47])=[O:7])[CH2:25][CH2:24]4)[CH2:21][CH2:20]3)=[CH:31][CH:32]=1)([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67776346HCID 67776346, compound

Product 1

HCID 71593638HCID 71593638, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 4-((1S,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(dimethylamino)ethylcarbamoyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (20 mg, 0.031 mmol) in DCM (2 mL) was added 3-chlorobenzoperoxoic acid (13.90 mg, 0.062 mmol) at −78° C. The reaction mixture was stirred for 3 hours. LCMS indicated the formation of desired product and consumption of the starting material. The reaction mixture was quenched with distilled water, extracted with DCM (3×2 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound as an yellow oil (10 mg, 49%). LCMS: m/e 661.49 (M+H)+, 2.79 min (method 1).

Workup

  1. customthe formation of desired product and consumption of the starting material
  2. customThe reaction mixture was quenched with distilled water
  3. extractionextracted with DCM (3×2 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97e5c5a42e7f41d291002a73b26c00fa
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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