Lithium Hydroxide → HCID 10230871, compound

HRID 24007Notes

Reaction equation

HRID 24007 reaction equation
C([O:3][C:4](=[O:43])[CH2:5][CH:6]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:30]=1)[N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[CH2:25][CH2:24][CH2:23][NH:22][C:21]=4[N:20]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)C.[OH-].[Li+].[Cl-].[NH4+]>C1COCC1.CO.O>[CH2:36]([O:35][C:31]1[CH:30]=[C:29]([CH:6]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][C:19]4[CH:28]=[CH:27][C:26]5[CH2:25][CH2:24][CH2:23][NH:22][C:21]=5[N:20]=4)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH2:5][C:4]([OH:43])=[O:3])[CH:34]=[CH:33][CH:32]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 67427468HCID 67427468, compound

Product 1

HCID 10230871HCID 10230871, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 3-(3-benzyloxy-phenyl)-3-{5-[2-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-indol-1-yl}-propionic acid ethyl ester (0.08 g, 0.14 mmol), lithium hydroxide (0.01 g, 0.22 mmol) and THF/methanol/water [2.0/1.0/0.2 mL] (3.2 mL) was microwave at 100° C. for 15 minutes. Saturated ammonium chloride was added (10 mL) and the product was extracted with ethyl acetate (3×10 mL). The crude product was purified via column chromatography eluting with dichloromethane: ethyl acetate (10:1) to give the title compound (25% yield) as white solid. 1H NMR (CDCl3) δ 10.5 (bs, 1H), 7.49 (d, 1H, J=3.0 Hz), 7.39-7.22 (m, 6H), 7.16 (m, 1H), 7.08 (m, 1H), 6.80 (m, 4H), 6.60 (dd, 1H, J=2.2, 6.8 Hz), 6.46 (m, 1H), 6.26 (d, 1H, J=7.3 Hz), 6.09 (m, 1H), 5.29 (s, 2H), 3.59 (s, 1H), 3.38 (m, 3H), 3.29-3.14 (m, 2H), 2.60-2.43 (m, 5H), 1.87 (m, 2H). Mass Spectrum (LCMS, ESI) calculated for C34H34N3O4 548.3 (M+H); found 548.4.

Workup

  1. extractionthe product was extracted with ethyl acetate (3×10 mL)
  2. customThe crude product was purified via column chromatography
  3. washeluting with dichloromethane: ethyl acetate (10:1)

Sources & evidence

ORD record
ord-34d178a7ed2c4e14bffee3a34cf63a34
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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