Hydrochloric Acid → HCID 68818026, compound

HRID 900333Notes

Reaction equation

HRID 900333 reaction equation
[OH-:1].[Na+].C[O:4][C:5](=[O:43])[CH:6](NC(OC(C)(C)C)=O)[CH2:7][S:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:27]4[O:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[C:26]=4[CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.Cl.[CH3:45][OH:46]>O1CCCC1.O>[C:10]([O:1][C:45]([C@H:6]([CH2:7][S:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:27]4[O:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[C:26]=4[CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[C:5]([OH:4])=[O:43])=[O:46])([CH3:15])([CH3:11])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 57588590HCID 57588590, compound

Product 1

HCID 68818026HCID 68818026, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2 N Sodium hydroxide solution (1.32 mL, 2.64 mmol) was added dropwise to a stirred solution of methyl-2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethylsulfanyl)propionate (500 mg, 0.88 mmol) in tetrahydrofuran (15 mL) and methanol (3 mL). The clear reaction mixture was stirred at room temperature until the reaction was complete (TLC control), and then diluted with water (10 mL), and acidified to pH 3 with 2 N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with water, sat'd aq NaCl, dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (5-10% methanol in methylene chloride) afforded the title compound has a white solid (420 mg), mp 205-206° C.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×20 mL)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over anhyd MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (5-10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-fc4d6f9fa096492cbc89f5ff88904a4f
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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