Methanol → HCID 21846484, compound

HRID 264015Notes

Reaction equation

HRID 264015 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]3([CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]([CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])[C:10]2=[O:28])=[CH:5][C:4]=1[C:29]([F:32])([F:31])[F:30])#[N:2].CO.[OH-].[Na+]>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[C:12]3([CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]([CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:10]2=[O:28])=[CH:5][C:4]=1[C:29]([F:30])([F:32])[F:31])#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 15345501Ethyl 3-(4-cyano-3-(trifluoromethyl)-phenyl)-2,4-dioxo-8-oxa-1,3-diazaspiro[4.5]decan-1-butanoate

Product 1

HCID 21846484HCID 21846484, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

522 mg of the product of Example 6 and 20 ml of methanol were mixed together and the solution was heated to 30° C., then returned to ambient temperatures 2 ml of 2N sodium hydroxide were added and the reaction medium stood for 4 hours and 30 minutes, then was poured into 30 ml of water and adjusted to pH 2-3. Extraction was carried out 3 times with ethyl acetate and the organic phase was washed with water, then with salt water, dried and purified on silica with methylene chloride-methanol: 9-1 as eluant. Then, solidification was carried out by trituration in 0.2 ml of isopropanol and 5 ml of ether to obtain 345 mg of the expected product (white crystals) melting at 151°-152° C.

Workup

  1. additionwere added
  2. extractionExtraction
  3. washthe organic phase was washed with water
  4. dry with materialwith salt water, dried
  5. custompurified on silica with methylene chloride-methanol

Sources & evidence

ORD record
ord-9a4cd4a9f081478f82a8056fea5e1d1a
Source dataset
uspto-grants-1997_07
Patent number
US05646172

Reaction notes

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