[(S)-3-Benzyloxy-1-(4-fluoro-2-phenylaminophenylcarbamoyl)propyl]carbamic acid tert-butyl ester → HCID 68157028, compound

HRID 242957Notes

Reaction equation

HRID 242957 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:19](=O)[NH:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C>Cl.O1CCOCC1>[CH2:12]([O:11][CH2:10][CH2:9][C@H:8]([NH2:7])[C:19]1[N:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:22]2[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:21]=2[N:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 68157459[(S)-3-Benzyloxy-1-(4-fluoro-2-phenylaminophenylcarbamoyl)propyl]carbamic acid tert-butyl ester

Product 1

HCID 68157028HCID 68157028, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of [(S)-3-benzyloxy-1-(4-fluoro-2-phenylaminophenylcarbamoyl)propyl]carbamic acid tert-butyl ester (1.22 g, 2.5 mmol) in 4M HCl in dioxane (10 mL) was heated at 70° C. for 2 h. After cooling to RT, the volatiles were concentrated in vacuo and the residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic fraction was washed with brine, dried (MgSO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford the title compound as a colourless oil (639 mg, 68%). LCMS (Method B): RT 2.11 and 2.55 min [M+H]+ 376.2.

Workup

  1. concentrationthe volatiles were concentrated in vacuo
  2. customthe residue partitioned between DCM
  3. washThe organic fraction was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-abc2f3409ecf446da4c84985d43fdce6
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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