Hydrochloric Acid → HCID 178452709, compound

HRID 1993555Notes

Reaction equation

HRID 1993555 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6](=O)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:10][CH:9]=1)C.[NH2:24][C:25]([NH2:27])=[S:26].CC(C)([O-])C.[K+].Cl>C(O)CCC.O>[C:18]([O:17][C:15](=[O:16])[NH:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]2[CH:5]=[C:4]([OH:3])[N:27]=[C:25]([SH:26])[N:24]=2)=[CH:9][CH:10]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2723790ThioureaHCID 23665647Potassium tert-butoxideHCID 586594254-(4-Tert-butoxycarbonylamino-phenyl)-3-oxo-butyric acid ethyl ester

Product 1

HCID 178452709HCID 178452709, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-(4-tert-butoxycarbonylamino-phenyl)-3-oxo-butyric acid ethyl ester (10.5 g, 32.7 mmol), thiourea (2.5 g, 32.7 mmol) and potassium tert-butoxide (8.3 g, 71.9 mmol, 2.2 equiv) in butan-1-ol (30 mL) is heated to 50° C. (oil bath temperature) for 23 h, under an argon atmosphere. The resulting yellow suspension is diluted with butan-1-ol (30 mL), neutralized by addition on 1N HCl (65 mL), diluted with H2O (20 mL) and extracted with CHCl3 (2×100 mL). The organic phase is dried (Na2SO4), filtered (washing the filter cake with copious amount of CHCl3) and concentrated in vacuo. After silica gel (300 g) column chromatography purification (CHCl3/MeOH, 90/10), the product is treated with CH2Cl2 (200 mL). The resulting suspension is allowed to stir at rt for 20 min, then diluted with hexane (200 mL) and filtered through a glass sintered funnel. The white residue is washed with a mixture (120 mL) of CH2Cl2/hexane (11, v/v) and dried in vacuo to afford the title compound: ES-MS: 334.0 [M+H]+; single peak at tR=7.04 min (System 2); Rf=0.34 (CHCl3/MeOH, 90/10).

Workup

  1. extractionextracted with CHCl3 (2×100 mL)
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered (
  4. washwashing the filter cake with copious amount of CHCl3) and
  5. concentrationconcentrated in vacuo
  6. customAfter silica gel (300 g) column chromatography purification (CHCl3/MeOH, 90/10)
  7. additionthe product is treated with CH2Cl2 (200 mL)
  8. additiondiluted with hexane (200 mL)
  9. filtrationfiltered through a glass sintered funnel
  10. washThe white residue is washed with a mixture (120 mL) of CH2Cl2/hexane (11
  11. customv/v) and dried in vacuo

Sources & evidence

ORD record
ord-27287129557d4836b0985eb3b07e5561
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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