Hydrochloric Acid → HCID 131727773, compound

HRID 1436327Notes

Reaction equation

HRID 1436327 reaction equation
C(OC(=O)[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:29])[NH2:28])=[C:23]([OH:30])[CH:22]=2)=[C:16]([F:31])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.[ClH:33]>ClCCl.O1CCOCC1>[ClH:33].[F:31][C:16]1[CH:15]=[C:14]([CH2:13][NH:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH:19]=[CH:18][C:17]=1[O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH2:28])=[O:29])=[C:23]([OH:30])[CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57939025HCID 57939025, compound

Product 1

HCID 131727773HCID 131727773, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

[4-(4-Carbamoyl-3-hydroxy-phenoxy)-3-fluoro-benzyl]-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-1e-1: 15 g) was dissolved in 150 mL of dichloromethane and treated with 50 mL of a 4.0 M hydrogen chloride solution in dioxane. After stirring 24 hours at room temperature, the volatiles were removed under reduced pressure and the resulting crude material was suspended in methanol, heated at reflux for 20 minutes, and stirred overnight at room temperature. The resulting slurry was collect via filtration, rinsed with chilled methanol, and dried under vacuum to provide the title compound (1A).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. temperatureheated
  3. temperatureat reflux for 20 minutes
  4. stirringstirred overnight at room temperature
  5. filtrationThe resulting slurry was collect via filtration
  6. washrinsed with chilled methanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6a7f32e087324ac29ea40f06fe04af55
Source dataset
uspto-grants-2009_11
Patent number
US07618996B2

Reaction notes

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