Hydrochloric Acid → HCID 178466790, compound

HRID 1161107Notes

Reaction equation

HRID 1161107 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-7eb5354051dd41fe9500a78b3d17520d
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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