Methanol → HCID 67178737, compound

HRID 1045047Notes

Reaction equation

HRID 1045047 reaction equation
CO.[C:3]([O:7][C:8](=[O:23])[CH2:9][CH2:10][N:11]([CH2:15][C:16]1[S:17][C:18]([CH2:21][CH3:22])=[CH:19][CH:20]=1)[C:12]([NH2:14])=[S:13])([CH3:6])([CH3:5])[CH3:4].CCO[C:27]([CH3:29])=O>>[C:3]([O:7][C:8](=[O:23])[CH2:9][CH2:10][N:11]([C:12]1[S:13][CH:15]=[C:16]([CH:20]2[CH2:19][CH:18]3[CH2:29][CH:27]2[CH2:22][CH2:21]3)[N:14]=1)[CH2:15][C:16]1[S:17][C:18]([CH2:21][CH3:22])=[CH:19][CH:20]=1)([CH3:5])([CH3:6])[CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 8857Ethyl Acetate2×HCID 592267203-[1-(5-Ethyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl ester

Product 1

HCID 67178737HCID 67178737, compoundYield 84%

Conditions

Temperature
60 °C

Procedure

Following a method analogous to General Procedure C, a portion of the above crude alpha-bromoketone (81 mg, 0.37 mmol) was added to a methanol (about 10 mL) solution of 3-[1-(5-ethyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl ester (122 mg, 0.371 mmol) and the reaction was heated at 60° C. and stirred overnight. The solvent was evaporated and ethyl acetate and saturated aq sodium bicarbonate solution were added to the residue. Extraction of the aq layer was performed two times with ethyl acetate. The combined organic portion was dried over sodium sulfate, and the dried solvent was decanted from the drying agent. The solvent was removed under reduced pressure to give the crude material. This was purified using silica gel chromatography (eluent: hexanes→19:1 hexanes:EtOAc→9:1 hexanes:EtOAc to give the purified 3-[(4-bicyclo[2.2.1]hept-2-yl-thiazol-2-yl)-(5-ethyl-thiophen-2-ylmethyl)-amino]-propionic acid tert-butyl ester (139 mg, 0.311 mmol, 84%) after evaporation of the eluent under reduced pressure.

Workup

  1. customThe solvent was evaporated
  2. additionethyl acetate and saturated aq sodium bicarbonate solution were added to the residue
  3. extractionExtraction of the aq layer
  4. dry with materialThe combined organic portion was dried over sodium sulfate
  5. customthe dried solvent was decanted from the drying agent
  6. customThe solvent was removed under reduced pressure
  7. customto give the crude material
  8. customThis was purified

Sources & evidence

ORD record
ord-a9aeb4162ab945e8badebab6c02d808f
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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