Hydrochloric Acid → HCID 22615024, compound

HRID 843182Notes

Reaction equation

HRID 843182 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][N:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[C:9]=2[C:10]=1[CH3:11])=[O:5])C.[OH-].[Li+].Cl.C(OCC)(=O)C>O1CCCC1.O>[C:31]([O:30][C:28]([N:20]([CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH2:19][CH2:18][CH2:17][O:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 57012649HCID 57012649, compound

Product 1

HCID 22615024HCID 22615024, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[3-(tert-Butoxycarbonyl-pyridin-3-ylmethyl-amino)-propoxy]-3-methyl-benzofuran-2-carboxylic acid ethyl ester (634 mg), the first intermediate of Example 87, was stirred with lithium hydroxide (113 mg) in tetrahydrofuran (2.7 ml) and water (2.7 ml) at 50° C. overnight. 2N HCl (1.35 ml) and ethyl acetate were added to the reaction mixture. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was obtained as a colorless foam (575 mg, 97%). The foam was used as a starting material in the next step without further purification. ESI-MS: m/z 441 (MH+); 1H-NMR δ: 1.51 (9H, s), 2.05-2.11 (2H, m), 2.74 (3H, s), 3.44 (2H, m), 4.02 (2H, t, J=5.4 Hz), 4,51 (2H, s), 6.51 (1H, d, J=7.6 Hz), 7.14 (1H, d, J=8.3 Hz), 7.23-7.34 (2H, m), 7.79 (1H, br), 8.51 (1H, dd, J=1.3, 5.0 Hz), 8.59 (1H, m).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3c5fda98db04308baf39e362af3c245
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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