Triethylamine → HCID 56847871, compound

HRID 1798417Notes

Reaction equation

HRID 1798417 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.[CH2:23](N)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]CC.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:6][CH2:5][CH2:4][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13583DodecylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 56847871HCID 56847871, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred yellow solution of VII (290.8 mg, 0.852 mmol) in anhydrous THF (10 mL) was added 1-dodecylamine (174 mg, 1.1×0.852 mmol) and then, dropwise, triethylamine (118 mg, 132 μL, 1.1×0.852 mmol). The solution was stirred for 3.5 hours at room temperature. The colorless solution was then diluted with diethylether 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 165 mg (48%) of a white solid, 10: mp=54-56° C. (uncorrected); Rf=0.61 (hexanes/ethyl acetate, 1:1, v/v); 1HNMR (CDCl3) δ 6.99 (d, 3J=8.0 Hz, 1H), 6.95 (d, 4J=1.55 Hz, 1H), 6.92 (bd, 3J=8.0 Hz, 1H), 5.04 (s, 2H), 4.69 (bs, 1H; NH), 3.82 (s, 3H), 3.17 (apparent quartet, 3J=6.7 Hz, 2H), 2.29 (s, 3H), 1.51-1.43 (m, 2H), 1.32-1.19 (m, 18H), and 0.86 (t, 3J=7 Hz, 3H). Exact mass (FAB+) calculated for C23H38NO5 [M+H] 408.2744. found 408.2749.

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-48b5565bcaa949589b0542f5d7a6794d
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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