Sodium Hydroxide → HCID 20817441, compound

HRID 897144Notes

Reaction equation

HRID 897144 reaction equation
[C:1]1([C:7]2([CH2:29][C:30]([O:32]CC)=[O:31])[CH2:9][CH:8]2[C:10]2[CH:15]=[CH:14][C:13]([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:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([C:7]2([CH2:29][C:30]([OH:32])=[O:31])[CH2:9][CH:8]2[C:10]2[CH:15]=[CH:14][C:13]([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:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20817472HCID 20817472, compound

Product 1

HCID 20817441HCID 20817441, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-phenyl-2-{4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}cyclopropylacetate (0.10 g ) in ethanol was added sodium hydroxide (10%, 5 mL) and was stirred for 24 h. The reaction mixture was concentrated and the residue was purified by hplc to afford 0.050 g of the desired product as its TFA salt. 1H NMR δ 7.58 (d, 1H, J=7.4 Hz), 7.39 (m, 2H), 7.28 (t, 2H, J=7.4 Hz), 7.22 (d, 2H, J=8.2 Hz), 7.16 (t, 1H, J=7.0 Hz), 6.88 (d, 2H, J=8.2 Hz), 6.72 (d, 1H, J=7.4 Hz), 4.27 (t, 2H, J=5.9 Hz), 3.49 (t, 2H, J=5.6 Hz), 3.14 (t, 2H, J=5.9 Hz), 2.81 (t, 2H, J=6.3 Hz), 2.44 & 1.93 (AB q, 2H, J=16.1 Hz), 2.30 (t, 1H, J=8.3 Hz), 1.91-1.94 (m, 2H), 1.42-1.54 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by hplc

Sources & evidence

ORD record
ord-405877330fb54b6c84a84a0f9e366bbe
Source dataset
uspto-grants-2005_07
Patent number
US06921767B2

Reaction notes

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