2-Ethylhexylamine → 4-{[(2-Ethylhexylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

HRID 1798416Notes

Reaction equation

HRID 1798416 reaction equation
S=C1N([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:20])[CH3:19])=[C:13]([O:21][CH3:22])[CH:12]=2)=[O:8])CCS1.[CH2:23]([CH:25]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:26][NH2:27])[CH3:24].C(N(CC)CC)C>C1COCC1.C(OCC)C>[C:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][O:9][C:7](=[O:8])[NH:27][CH2:26][CH:25]([CH2:23][CH3:24])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 77192-EthylhexylamineHCID 8471TriethylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 568478734-{[(2-Ethylhexylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred yellow solution of VII (298.2 mg, 0.873 mmol) in anhydrous THF (10 mL) was added 2-ethylhexylamine (124 mg, 157 μL 1.1×0.873 mmol) and then, dropwise, triethylamine (97 mg, 135 μL, 1.1×0.873 mmol). The solution was stirred for 3 hours at room temperature. The colorless solution was then diluted with diethyl ether and washed with 1N HCl, distilled water, and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate (6:4, v/v) to give 9 as 207.2 mg (68%) of a clear, light yellow oil: Rf=0.60 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 6.99 (d, 3J=8.0 Hz, 1H), 6.95 (d, 4J=1.75 Hz, 1H), 6.92 (dd, 3J=8.0 Hz, 4J=1.72 Hz, 1H), 5.04 (s, 2H), 4.67 (bs, 1H, NH), 3.82 (s, 3H), 3.16-3.08 (m, 2H), 2.29 (s, 3H), 1.43-1.35 (m, 1H), 1.33-1.119 (m, 8H) and 0.867 (apparent triplet, 3J=7.2 Hz, 6H). Exact mass (FAB+) calculated for C19H30NO5 [M+H] 352.2118. found 352.2101.

Workup

  1. washwashed with 1N HCl
  2. distillationdistilled water, and saturated NaCl
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica gel
  7. customto give 9 as 207.2 mg (68%) of a clear, light yellow oil

Sources & evidence

ORD record
ord-7139a8782e68454ebeebf8f1c6904d58
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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