Hydrochloric Acid → HCID 178466790, compound

HRID 1717794Notes

Reaction equation

HRID 1717794 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[C:6]([C:9]1[CH:39]=[CH:38][C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([O:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)[C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25](O)=O)=[CH:17][CH:16]=2)=[C:11]([CH3:40])[C:10]=1[OH:41])(=[O:8])[CH3:7].[OH-].[K+].Cl>CC(C)=O.O>[OH:41][C:10]1[C:11]([CH3:40])=[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]([C:22]3[CH:30]=[CH:29][CH:28]=[C:24]([C:25]4[NH:5][C:3]([SH:4])=[N:2][N:1]=4)[CH:23]=3)[O:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][O:33]3)=[CH:17][CH:16]=2)[CH:38]=[CH:39][C:9]=1[C:6](=[O:8])[CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86620600HCID 86620600, compound

Product 1

HCID 178466790HCID 178466790, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Heat a solution of 3-[[4-(4-acetyl-3-hydroxy-2-methyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzoic acid thiosemicarbazide (1.20 g, 2.04 mmol) and potassium hydroxide (0.228 g, 4.08 mmol) in acetone (5.0 mL) and water (5.0 mL) overnight. Acidify with 2N hydrochloric acid and extract with ethyl acetate (5×). Combine organic layers and wash with brine, dry, and concentrate to afford the title compound which was used without further purification (1.12 g, 2.04 mmol, 99%). MS (m/z): 544 (M−H).

Workup

  1. extractionextract with ethyl acetate (5×)
  2. washCombine organic layers and wash with brine
  3. customdry
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-171d9aec419a46fda78cb5a138c8ca0d
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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