Hydrochloric Acid → HCID 117824033, compound

HRID 59125Notes

Reaction equation

HRID 59125 reaction equation
[Na].[CH:2]1([CH2:5][O:6][CH2:7][C:8](=O)[CH2:9][C:10]([O:12]CC)=O)[CH2:4][CH2:3]1.[NH2:16][C:17]([NH2:19])=[S:18].Cl>CCO>[CH:2]1([CH2:5][O:6][CH2:7][C:8]2[NH:19][C:17](=[S:18])[NH:16][C:10](=[O:12])[CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723790ThioureaHCID 5360545SodiumHCID 63897208Ethyl 4-(cyclopropylmethoxy)-3-oxobutanoate

Product 1

HCID 117824033HCID 117824033, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (4.0 g, 172 mmol) was added to EtOH (80 mL) and stirred until all dissolved at 60° C. The solution was cooled down to rt and a solution of ethyl 4-(cyclopropylmethoxy)-3-oxobutanoate (15.7 g, 78.4 mmol) in EtOH (80 mL) was added, followed by thiourea (7.2 g, 94 mmol). The mixture was stirred under reflux conditions for 24 h. Hydrochloric acid (aq, 1 M) was added until pH˜4 and the mixture was concentrated in vacuo. The residue was purified by column chromatography on silica eluting with a gradient of EtOAc and DCM to give the title compound as a solid, 15.7 g (95%).

Workup

  1. dissolutionall dissolved at 60° C
  2. stirringThe mixture was stirred under reflux conditions for 24 h
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was purified by column chromatography on silica eluting with a gradient of EtOAc and DCM

Sources & evidence

ORD record
ord-f9b6fd8e4fdc4b49abd347466603bf4c
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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