Hydrochloric Acid → HCID 59696199, compound

HRID 900347Notes

Reaction equation

HRID 900347 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:36])[C@@H:6]([NH2:35])[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>O1CCCC1.CO>[NH2:35][C@@H:6]([CH2:7][S:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][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:20][CH:21]=2)=[CH:12][CH:11]=1)[C:5]([OH:36])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68827544HCID 68827544, compound

Product 1

HCID 59696199HCID 59696199, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2N Sodium hydroxide (0.5 mL) was added to a stirred solution of the amino methyl ester, (2R)-Methyl-2-Amino-3-(4′-dibenzofuran-4-ylbipheny-4-ylmethylsulfanyl)-propionate (100 mg) in a mixture of tetrahydrofuran (5 mL) and methanol (1 mL). The solution was stirred for 1 hour and then acidified to pH 3 with 2N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (3×10 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 25% methanol in methylene chloride as eluent, afforded the title compound as a cream solid (83 mg, 86%); Rf: 0.10 (25% methanol in dichloromethane); 1H NMR (DMSO-d6, 300 MHz): δ 11.20 (3H, br s, NH, OH), 7.94 (1H, d, J=9 Hz, Ar—H), 7.91 (1H, d, J=8 Hz, Ar—H), 7.86 (2H, d, J=9 Hz, Ar—H), 7.67 (2H, d, J=9 Hz, Ar—H), 7.48-7.57 (4H, m, Ar—H), 7.21-7.39 (5H, m, Ar—H), 4.02 (1H, dd, J=8, 5 Hz, CHN), 3.74 (2H, s, PhCH2S), 2.94 (1H, dd, J=16, 5 Hz, CHHCHN), 2.86 (1H, dd, J=16, 8 Hz, CHHCHN); ESI-LCMS e/z calcd for C28H23NO3S 453.560, found 454 (M+H)+.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×10 mL)
  2. extractionThe combined extract
  3. washwas washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the product by flash column chromatography

Sources & evidence

ORD record
ord-596cc7b3ab6442e8b7b7eeac29af4e23
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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