Triethylamine → HCID 86592526, compound

HRID 1374426Notes

Reaction equation

HRID 1374426 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][C:7]([C:9]2[N:10]=[C:11]([SH:14])[S:12][CH:13]=2)=[CH:6][CH2:5][N:4]1[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16].[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[OH:1][CH2:2][C@@H:3]1[CH2:8][C:7]([C:9]2[N:10]=[C:11]([S:14][CH2:27][C:26]3[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[S:12][CH:13]=2)=[CH:6][CH2:5][N:4]1[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 516892Sodium BicarbonateHCID 178459663HCID 178459663, compound

Product 1

HCID 86592526HCID 86592526, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (2S)-2-(hydroxymethyl)-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (218 mg, 0.7 mmol) in THF (3 ml) were added at 0–5° C. 4-methoxybenzyl chloride (95 ml, 0.70 mmol) and triethylamine (98 ml, 0.7 mmol). The mixture was stirred for 3 hours and then at room temperature for 45 minutes. To the solution were added an aqueous sodium hydrogen carbonate solution and ethy acetate. The mixture was separated with a separating funnel. The organic layer was washed with a saturated aqueous sodium solution, dried over magnesium sulfate and the organic layer was removed in vacuo. The residue was purified with preparative TLC to give allyl (2S)-2-(hydroxymethyl)-4-{2-[(4-methoxybenzyl)sulfanyl]-1,3-thiazol-4-yl}-3,6-dihydro-1(2 H)-pyridinecarboxylate (150 mg, 50%).

Workup

  1. waitat room temperature for 45 minutes
  2. customThe mixture was separated with a separating funnel
  3. washThe organic layer was washed with a saturated aqueous sodium solution
  4. dry with materialdried over magnesium sulfate
  5. customthe organic layer was removed in vacuo
  6. customThe residue was purified with preparative TLC

Sources & evidence

ORD record
ord-897472390af24eeda396314dbff1b03e
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

Loading…