Ethylamine → HCID 56847973, compound

HRID 1798424Notes

Reaction equation

HRID 1798424 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.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][CH3:4])=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 56847973HCID 56847973, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of VII (207 mg, 0.606 mmol), ethylamine (2M in THF, 31.5 mg, H2NEt, 350 μL of solution, 1.16×0.606 mmol H2NEt) and triethylamine (122 mg, 169 μL, 2×0.606 mmol) anhydrous THF (3 mL, 5 mL/mmol of 6) was stirred for one hour. The reaction mixture was diluted with CH2Cl2 and extracted with 1N HCl 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 CH2Cl2/ethyl acetate (94:6, v/v) to give 114.1 mg (70%) of 18 as an oil: Rf=0.37 (CH2Cl2/EtOAc, 96:4, v/v); 1HNMR (CDCl3) δ 6.98 (d, 3J=8 Hz, 1H), 6.95 (bs, 1H), 6.92 (bd, 3J=8 Hz, 1H), 5.04 (bs, 2H), 4.68 (bs, 1H), 3.82 (s, 3H), 3.22 (m, 2H) and 1.13 (t, 3J=7.25 Hz, 3H). Exact mass (ESI) calculated for C13H18NO5 [M+H]=268.1179. found 268.1189.

Workup

  1. extractionextracted with 1N HCl and saturated NaCl
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d91cd18b4da74f2f9c61f5315ecec524
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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