Diazoethane → HCID 57941618, compound

HRID 1437593Notes

Reaction equation

HRID 1437593 reaction equation
[N+:1]([O:4][CH:5]([CH2:33][O:34][N+:35]([O-:37])=[O:36])[CH2:6][O:7][C:8]([O:10][CH2:11]/[C:12](/[C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[C:13](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)\[C:14]([OH:16])=[O:15])=[O:9])([O-:3])=[O:2].[N+](=[CH:40][CH3:41])=[N-]>C1COCC1.C(OCC)C>[N+:1]([O:4][CH:5]([CH2:33][O:34][N+:35]([O-:37])=[O:36])[CH2:6][O:7][C:8]([O:10][CH2:11]/[C:12](/[C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:27][CH:28]=1)=[C:13](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)\[C:14]([O:16][CH2:40][CH3:41])=[O:15])=[O:9])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 70695DiazoethaneHCID 57941613HCID 57941613, compound

Product 1

HCID 57941618HCID 57941618, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 454 mg of (2Z)-4-({[2,3-bis(nitrooxy)propoxy]carbonyl}oxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 20 mL of THF was added excess diazoethane in diethylether until crude NMR revealed complete conversion to ethyl ester. Evaporation of the solvent followed by flash chromatography of the crude residue over silica gel (30-90% EtOAc/hexane) afforded 420 mg of the title compound as a clear colourless oil. 1H NMR (500 MHz, acetone-d6): δ 7.80 (d, 2H), 7.49 (d, 2H), 7.23-7.18 (m, 3H), 7.14-7.08 (m, 2H), 5.79-5.73 (m, 1H), 5.35 (s, 2H), 5.05 (dd, 1H), 4.85 (dd, 1H), 4.64 (dd, 1H), 4.47 (dd, 1H), 4.31 (q, 2H), 3.08 (s, 3H), 1.29 (t, 3H).

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-338651c4ef3c4367b7022d9f210fdd7e
Source dataset
uspto-grants-2009_11
Patent number
US07622501B2

Reaction notes

Loading…