Benzylamine → 4-{[(Benzylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetate

HRID 1798415Notes

Reaction equation

HRID 1798415 reaction equation
S=C1[N:6]([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])[CH2:5][CH2:4]S1.C(N)[C:24]1[CH:29]=[CH:28]C=[CH:26][CH:25]=1>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:6][CH2:5][C:4]2[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=2)=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 568479164-{[(Benzylcarbamoyl)oxy]methyl}-2-methoxyphenyl acetateYield 7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Compound VII (339 mg, 0.993 mmol) was dissolved in anhydrous THF (5 mL). To the stirred, yellow solution was added at room temperature a solution of benzylamine (160 mg, 163 pt, 1.5×0.993 mmol) in anhydrous THF (5 mL), After being stirred overnight, the reaction solution was diluted with diethyl ether and extracted with 1N HCl, water and saturated NaCl. The organic phase was dried over anhydrous MgSO4, filtered and concentrated. Purification by column chromatography on silica gel eluting with hexanes/ethyl acetate (7:3-1:1, v/v) afforded 23 mg (7%) of 8 as a clear oil: Rf=0.30 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 7.34-7.25 (m, 5H), 6.99 (d, 3J=8.0 Hz, 1H), 6.96 (s, 1H), 6.92 (d, 3J=8.1 Hz, 1H), 5.09 (s, 2H), 5.04 (bs, 1H, NH), 4.38 (d, 3J=6 Hz, 2H), 3.81 (s, 3H) and 2.29 (s, 3H). While the synthesis proceeded in excellent yield, product isolation was compromised by decomposition during work-up.

Workup

  1. extractionextracted with 1N HCl, water and saturated NaCl
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel eluting with hexanes/ethyl acetate (7:3-1:1

Sources & evidence

ORD record
ord-2e82cd9608034f37880878757b951764
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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