Water → HCID 86592527, compound

HRID 1374427Notes

Reaction equation

HRID 1374427 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][C:7]([C:9]2[N:10]=[C:11]([S:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[S:12][CH:13]=2)=[CH:6][CH2:5][N:4]1[C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25].ClS([N:34]=[C:35]=[O:36])(=O)=O.O.C(OCC)(=O)C>C(Cl)(Cl)Cl>[NH2:34][C:35]([O:1][CH2:2][C@@H:3]1[CH2:8][C:7]([C:9]2[N:10]=[C:11]([S:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[S:12][CH:13]=2)=[CH:6][CH2:5][N:4]1[C:24]([O:26][CH2:27][CH:28]=[CH2:29])=[O:25])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70918Chlorosulfonyl isocyanate2×HCID 86592526HCID 86592526, compound

Product 1

HCID 86592527HCID 86592527, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of allyl (2S)-2-(hydroxymethyl)-4-{2-[(4-methoxybenzyl)sulfanyl]-1,3-thiazol-4-yl}-3,6-dihydro-1(2 H)-pyridinecarboxylate (75 mg, 0.17 mmol) in chloroform (1 ml) was added at 0–5° C. chlorosulfonylisocyanate (17 ml, 0.20 mmol). Three hours later, chlorosulfonylisocyanate (10 ml, 0.11 mmol) was further added thereto. Three hours later, to the mixture was added water and the mixture was stirred for 10 minutes. To the solution was added ethyl acetate and the solution was separated with a separating funnel. The organic layer was washed with a saturated aqueous sodium chloride 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-{[(aminocarbonyl)oxy]methyl}-4-{2-[(4-methoxybenzyl)sulfanyl]-1,3-thiazol-4-yl}-3,6-dihydro-1(2 H)-pyridinecarboxylate (74.5 mg, 90%).

Workup

  1. customthe solution was separated with a separating funnel
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customthe organic layer was removed in vacuo
  5. customThe residue was purified with preparative TLC

Sources & evidence

ORD record
ord-ea93b513ba8c4096b57bc72352ce3ace
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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