Hydrochloric Acid → HCID 69064618, compound

HRID 1435081Notes

Reaction equation

HRID 1435081 reaction equation
C(OC(=O)[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH2:27])=[CH:22][C:21]=2[CH3:29])=[CH:16][C:15]=1[Cl:30])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.[ClH:32]>C(OCC)(=O)C.O1CCOCC1.CO>[ClH:30].[Cl:32][C:22]1[C:21]([CH3:29])=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([CH2:13][NH:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:15][CH:16]=2)[CH:25]=[CH:24][C:23]=1[C:26]([NH2:27])=[O:28]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57937832HCID 57937832, compound

Product 1

HCID 69064618HCID 69064618, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

(4′-Carbamoyl-3-chloro-2′-methyl-biphenyl-4-ylmethyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-3e: 12.6 g, 28.3 mmol) was dissolved in ethyl acetate and treated with 30 ml of 4.0M hydrogen chloride in dioxane. After stirring for 24 hours at room temperature, the volatiles were removed under reduced pressure and the product was isolated by dissolving the crude material in methanol and slowly adding ethyl acetate to precipitate the product, which was isolated via filtration. The solid was crystallized by dissolving in 10 parts of hot ethanol before cooling to room temperature. After stirring for 48 hours, the resulting slurry was collected via filtration, rinsing with chilled ethanol, to provide the title compound (E3-01) as a colorless solid.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe product was isolated
  3. customto precipitate the product
  4. customwhich was isolated via filtration
  5. customThe solid was crystallized
  6. dissolutionby dissolving in 10 parts of hot ethanol
  7. temperaturebefore cooling to room temperature
  8. stirringAfter stirring for 48 hours
  9. filtrationthe resulting slurry was collected via filtration
  10. washrinsing with chilled ethanol

Sources & evidence

ORD record
ord-35b22894195e436e97a30eacaac1f679
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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