Water → HCID 44250417, compound

HRID 1619153Notes

Reaction equation

HRID 1619153 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]1([CH2:15][NH:16][C:17](=[O:41])[C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[C:28]4[NH:30][C:31](=[O:38])[C:32]5([CH2:37][CH2:36][S:35][CH2:34][CH2:33]5)[C:27]4=[CH:26][CH:25]=3)[C:21]([CH3:39])=[C:20]([F:40])[CH:19]=2)[CH2:14][CH2:13]1.[OH2:42]>ClCCl>[CH:12]1([CH2:15][NH:16][C:17](=[O:41])[C:18]2[CH:19]=[C:20]([F:40])[C:21]([CH3:39])=[C:22]([C:24]3[CH:29]=[C:28]4[NH:30][C:31](=[O:38])[C:32]5([CH2:37][CH2:36][S:35](=[O:9])(=[O:42])[CH2:34][CH2:33]5)[C:27]4=[CH:26][CH:25]=3)[CH:23]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acid2×HCID 67269424HCID 67269424, compound

Product 1

HCID 44250417HCID 44250417, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-chloroperbenzoic acid (0.04 g, 0.23 mmol) was added portionwise to a solution of N-(cyclopropylmethyl)-3-fluoro-4-methyl-5-(2-oxo-1,2,2′,3′,5′,6′-hexahydrospiro-[indole-3,4′-thiopyran]-6-yl)benzamide (example 28a, 0.10 g, 0.24 mmol) in dichloromethane (4 mL) at 0° C. The mixture was warmed to ambient temperature. After 2 hours, the mixture was cooled to 0° C. and further 3-chloroperbenzoic acid (0.04 g, 0.23 mmol) was added portionwise and the resulting mixture was stirred at room temperature for 1 additional hour. Water and dichloromethane were added, the organic layer was separated and washed with a 4% aqueous sodium hydrogen carbonate solution, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was triturated with diethyl ether to yield the title compound (0.09 g, 79%) as a white solid.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. customthe organic layer was separated
  3. washwashed with a 4% aqueous sodium hydrogen carbonate solution
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-3a40b6578d0649f498906d60033b2835
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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