Hydrochloric Acid → HCID 69325334, compound

HRID 2054593Notes

Reaction equation

HRID 2054593 reaction equation
C[O:2][C:3](=[O:42])[C@@H:4]1[CH2:8][CH:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:27]5[O:28][C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=6[C:26]=5[CH:25]=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][N:5]1[C:35]([O:37]C(C)(C)C)=[O:36].[OH-].[K+].Cl.[CH2:46]1[CH2:50]O[CH2:48][CH2:47]1>CO.C(OCC)(=O)C>[CH:25]1[C:26]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[O:28][C:27]=2[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:13]3[CH:12]=[CH:11][C:10]([O:9][CH:7]4[CH2:6][N:5]([C:35]([O:37][CH2:50][CH2:46][CH2:47][CH3:48])=[O:36])[C@H:4]([C:3]([OH:2])=[O:42])[CH2:8]4)=[CH:15][CH:14]=3)=[CH:17][CH:18]=2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 69326674HCID 69326674, compound

Product 1

HCID 69325334HCID 69325334, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4′-dibenzofuran-4-yl-bipheny-4-yloxy)-N-tert-butoxycarbonyl-proline methyl ester (400 mg, 0.71 mmol) in THF (3 mL) and methanol (4 mL) was cooled to 0° C. and treated with 2 N KOH (1.25 mL). After stirring at room temperature for 1 H the solution was acidified with 10% HCl to pH 2 and diluted with 25ml of ethyl acetate. After being separated, 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 4-(4′-dibenzofuran-4-yl-bipheny-4-yloxy)-N-butoxycarbonyl-proline (320 mg, 82%) as pale yellow solid. 0.320 g (yield 82.1%). 1H NMR (DMSO-d6), δ 8.16 (dd, J=8, 12 Hz, 2H), 7.98 (d, J=9 Hz, 2H), 7.80 (m, 6H), 7.47 (m, 3H), 6.97 (d, J=9 Hz, 2H), 5.08 (m, 1H), 4.29 (t, J=9 Hz, 1H), 3.72 (m, 1H), 3.42 (dd, J=6, 9 Hz, 1H), 2.62 (m, 1H), 2.20 (m, 1H), 1.44 (s, 9H). LCMS 450 (M+−100).

Workup

  1. customAfter being separated
  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-50941fd32b6f4c0381eaf358eb08948d
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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