Hydrochloric Acid → 2-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid

HRID 900379Notes

Reaction equation

HRID 900379 reaction equation
C[O:2][C:3](=[O:40])[CH:4]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:24]4[O:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:23]=4[CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[OH-].[K+].Cl>C1COCC1.CO.C(OCC)(=O)C>[C:36]([O:35][C:33]([NH:32][CH:4]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:24]4[O:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:23]=4[CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[C:3]([OH:40])=[O:2])=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1317268282-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid methyl ester

Product 1

HCID 113647022-tert-Butoxycarbonylamino-3-(4'-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acidYield 75.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-tert-Butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid methyl ester (0.150 g, 0.27 mmol) in THF (2 mL) and methanol (2 mL) was cooled to 0° C. and treated with 2 N KOH (1.0 mL). After stirring at room temperature for 1 h the solution was acidified with 10% HCl to pH 2 and diluted with ethyl acetate (25 mL). After being seperated, the aqueous layer was extracted with ethyl acetate (3×15 mL) and the combined organic layers were dried over MgSO4 and concentrated. Purification by flash column chromatography (2-5% methanol in dichloromethane) provided 2-tert-Butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphen-4-ylsulfanyl)-propanoic acid (110 mg, 75%) as white solid. 1H NMR (CDCl3), δ 8.18 (d, J=7 Hz, 2H), 8.14 (dd, J=1, 7 Hz, 2H), 7.98 (d, J=9 Hz, 2H), 7.82 (d, J=9 Hz, 2H), 7.72 (m, 4H), 7.51 (m, 3H), 3.90 (m, 1H), 3.48 (dd, J=4, 12 Hz, 1H), 3.30 (m, 1H), 1.47 (s, 9H). LCMS 440 (M+−100).

Workup

  1. customAfter being seperated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×15 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (2-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-40ad8b720644428c99ad60ac97871464
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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