Hydrochloric Acid → HCID 60029921, compound

HRID 496416Notes

Reaction equation

HRID 496416 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13](=[O:41])[NH:14][CH2:15][C:16]1[C:25]2[CH2:24][CH2:23][CH2:22][C:21](=[O:26])[C:20]=2[CH:19]=[CH:18][C:17]=1[O:27][C@@H:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:29][N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1)[CH2:9][CH2:10][S:11][CH3:12])(C)(C)C.Cl>CO.O1CCOCC1>[NH2:7][C@@H:8]([CH2:9][CH2:10][S:11][CH3:12])[C:13]([NH:14][CH2:15][C:16]1[C:25]2[CH2:24][CH2:23][CH2:22][C:21](=[O:26])[C:20]=2[CH:19]=[CH:18][C:17]=1[O:27][C@@H:28]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH2:29][N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1)=[O:41]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60029912HCID 60029912, compound

Product 1

HCID 60029921HCID 60029921, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ((S)-1-{[2-((S)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-ylmethyl]-carbamoyl}-3-methylsulfanyl-propyl)-carbamic acid tert-butyl ester (153 mg, 0.258 mmol) in MeOH (1 mL) was added 4 M HCl in dioxane (3 mL). The mixture was concentrated after 3 h. The residue was neutralized with aqueous NaHCO3 and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a pale yellow oil. Purification by chromatography (5% MeOH/CH2Cl2 with 1% NH4OH) afforded the title compound as a white foam (76 mg, 0.154 mmol, 60%).

Workup

  1. concentrationThe mixture was concentrated after 3 h
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a pale yellow oil
  7. customPurification by chromatography (5% MeOH/CH2Cl2 with 1% NH4OH)

Sources & evidence

ORD record
ord-124cc6e763e74a01bf9404fc12fda627
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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