Hydrochloride methanol → HCID 67255827, compound

HRID 1752014Notes

Reaction equation

HRID 1752014 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH:7]2[C:11]([CH2:13][N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)([OH:12])[C:10]([CH2:20][O:21]COC)([CH3:19])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.CO>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:11]([CH2:13][N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)([OH:12])[C:10]([CH2:20][OH:21])([CH3:19])[CH2:9][CH2:8]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 67256764HCID 67256764, compound

Product 1

HCID 67255827HCID 67255827, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Chlorobenzyl)-2-methoxymethoxymethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (Compound (VII), R1=CH3, Ym=4-Cl, G=CH2OCH3, A=N) (629 mg, 1.66 mmol) was dissolved in methanol (6.3 ml), 10% hydrogen chloride-methanol (6.3 ml, 1.73 mmol) was added and stirring was conducted at room temperature for 48 hours. After completion of the reaction, the solvent was distilled away, and water was added. After ethyl acetate (80 ml) was added, an aqueous solution of sodium hydroxide was added until the pH became 10. The organic layer was separated, washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled away to obtain the title compound (VI-1 (Compound (VI), (Ra2)Xa2na2(OH)pa1=CH3, (Rb2)Xb2nb2(OH)pb1=CH2OH, Ym=4-Cl, A=N, isomer type: C): VI-2 (Compound (VI), (Ra2)Xa2na2(OH)pa1=CH2OH, (Rb2)Xb2nb2(OH)pb1=CH3, Ym=4-Cl, A=N, isomer type: C): other isomers (isomer type: T)=6:3:1).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled away
  3. additionwater was added
  4. additionAfter ethyl acetate (80 ml) was added
  5. additionan aqueous solution of sodium hydroxide was added until the pH
  6. customThe organic layer was separated
  7. washwashed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-1f1aea0b9a4e4ed1b1e2519d248c4c0c
Source dataset
uspto-grants-2015_10
Patent number
US09162966B2

Reaction notes

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