Hydrochloric Acid → HCID 68818026, compound

HRID 900343Notes

Reaction equation

HRID 900343 reaction equation
[OH-:1].[Na+].C[O:4][C:5](=[O:43])[C@@H: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 68819599HCID 68819599, compound

Product 1

HCID 68818026HCID 68818026, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2N Sodium hydroxide solution (1.32 mL, 2.64 mmol) was added dropwise to a stirred solution of (2R)-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 2N hydrochloric acid. The reaction mixture was extracted with ethyl acetate (2×20 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 5-10% methanol in methylene chloride as eluent, afforded the title compound has a white solid (420 mg, 87%), m.pt. 205-206° C.; Rf: 0.40 (10% methanol in dichloromethane); 1H NMR (MeOH-d4): δ 7.90 (4H, m, Ar—H), 7.67 (2H, d, J=9 Hz, Ar—H), 7.56 (2H, d, J=9 Hz, Ar—H), 7.53 (2H, d, J=8 Hz, Ar—H), 7.29-7.41 (5H, m, Ar—H), 4.34 (1H, m, CHN), 3.87 (2H, s, PhCH2S), 2.95 (1H, dd, J=15, 5 Hz, CHHCHN), 2.86 (1H, dd, J=15, 7 Hz, CHHCHN), 1.42 (9H, s, CMe3); ESI-LCMS e/z calcd for C33H31NO5S 553.676, found 554 (M+H)+, 576 (M+Na)+.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×20 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-40c96c90c99b4a44951fec337ace7051
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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