Tetrahydrofuran → 7-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

HRID 985492Notes

Reaction equation

HRID 985492 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]4[C:28]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[CH:27][S:26][C:25]=4[CH:36]=3)[N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Na+]>O>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]4[C:28]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][S:26][C:25]=4[CH:36]=3)[N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 695481007-{2-[3-(2-Ethoxycarbonyl-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 695482037-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl esterYield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-{2-[3-(2-Ethoxycarbonyl-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (338 mg, 0.66 mmol) was dissolved THF (5ml). Then a solution of sodium hydroxide (132 mg, 3.30 mmol) in water (1 ml) was added. The reaction was stirred at room temperature for 16 hours. After that period, the solvent was evaporated under vacuum and the crude was extracted with ethyl acetate and hydrochloric acid (1M). The organic layer was collected, dried with anhydrous sodium sulfated, filtrated and evaporated under vacuum to yield 268 mg (84%) of 7-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester. NMR 1H Cl3CD δ: 7.59 (d, 1H, J=8.8 Hz), 7.47 (d, 1H, J=7.7 Hz), 7.35 (d, 1H, J=2.3 Hz), 7.05 (d, 1H, J=7.6 Hz), 7.01 (s, 1H), 6.96 (dd, 1H, J=2.3, 8.8 Hz), 4.35 (t, 2H, J=6.5 Hz), 3.73 (m, 2H), 3.18 (m, 2H), 3.05 (m, 2H), 2.72 (m, 2H), 2.66 (m, 2H), 1.88 (m, 2H), 1.49 (s, 9H).

Workup

  1. waitAfter that period
  2. customthe solvent was evaporated under vacuum
  3. extractionthe crude was extracted with ethyl acetate and hydrochloric acid (1M)
  4. customThe organic layer was collected
  5. dry with materialdried with anhydrous sodium
  6. filtrationfiltrated
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-0f5c6c02972046fbb10c0e1e7c06b09d
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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