Ethyl 1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxylate → N-[2-(aminosulfonyl)-4-(benzyloxy)phenyl]-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxamide

HRID 494446Notes

Reaction equation

HRID 494446 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:15][CH2:16][CH3:17])([CH2:12][CH2:13][CH3:14])[C:4](=[O:18])[C:3]=1[C:19](OCC)=[O:20].[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][C:26]=1[S:39]([NH2:42])(=[O:41])=[O:40]>C1(C)C=CC=CC=1>[NH2:42][S:39]([C:26]1[CH:27]=[C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:30][C:25]=1[NH:24][C:19]([C:3]1[C:4](=[O:18])[C:5]([CH2:15][CH2:16][CH3:17])([CH2:12][CH2:13][CH3:14])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[OH:1])=[O:20])(=[O:40])=[O:41]

Participants

4

Reactant 2

HCID 54724640Ethyl 1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxylateHCID 670639862-Amino-5-(benzyloxy)benzenesulfonamide

Product 1

HCID 68871690N-[2-(aminosulfonyl)-4-(benzyloxy)phenyl]-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxamideYield 102.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of the product of Example 1F (617 mg, 1.95 mmol) and the product of Example 2D (542 mg, 1.95 mmol) in toluene (20 mL) was stirred at reflux for 18 hours and concentrated in vacuo to afford the title compound (1.1 g, 100%). 1H NMR (300 MHz, CDCl3): δ 17.85 (d, J=12.13 Hz, 1 H), 12.49 (s, 1 H), 12.35 (s, 1 H), 8.32 (d, J=6.62 Hz, 1 H), 8.18 (m, 1 H), 7.98 (d, J=9.19 Hz, 1 H), 7.66 (m, 2 H), 7.42 (m, 3 H), 7.27 (m, 4 H), 5.49 (s, 1 H), 5.37 (s, 1 H), 5.07 (d, J=30.89 Hz, 2 H), 2.31 (m, 2 H), 1.86 (m, 2 H), 0.94 (m, 2 H), 0.72 (m, 8 H).

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5626314ccf94e06965f798fad545c5d
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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