Triethylamine → HCID 56847913, compound

HRID 1798420Notes

Reaction equation

HRID 1798420 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.[CH:23]1(CN)[CH2:28][CH2:27]C[CH2:25][CH2:24]1.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[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][CH:4]2[CH2:27][CH2:28][CH2:23][CH2:24][CH2:25]2)=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 56847913HCID 56847913, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred yellow solution of VII (293.8 mg, 0.861 mmol) in anhydrous THF (10 mL) was added cyclohexylmethanamine (165 mg, 123 μL, 1.1×0.861 mmol) and then, dropwise, triethylamine (96 mg, 133 μL, 1.1×0.861 mmol). The solution was stirred for 45 minutes at room temperature. The colorless solution was then diluted with CH2Cl2 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 (1:1, v/v) to yield 150.2 mg (52%) of 13 as a clear colorless oil: Rf=0.55 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 6.98 (d, 3J=8.0 Hz, 1H), 6.95 (d, 1H), 6.91 (dd, 3J=8.0 Hz, 1H), 5.04 (s, 2H, CH2O), 4.75 (bs, 1H, NH), 3.81 (s, 3H, OCH3), 3.01 (t, 3J=6.4 Hz, 211, NCH2), 2.29 (s, 3H), 1.70-1.62 (m, 5H), 1.42 (bs, 1H), 1.23-1.11 (m, 3H) and 0.92 (q, 3J=11.5 Hz, 2H).

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

Sources & evidence

ORD record
ord-14c4664da6a448e69338489f3159c1d2
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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