HCID 14353611, compound → HCID 68655055, compound

HRID 1861244Notes

Reaction equation

HRID 1861244 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[NH:10][N:9]=[C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[S:7]1)=[O:5])[CH3:2].[CH:15]1[C:27]2[CH:26]([CH2:28][O:29][C:30](=[O:39])[NH:31][CH:32]([C:36](Cl)=[O:37])[CH:33]([CH3:35])[CH3:34])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[N:10]([C:36](=[O:37])[CH:32]([NH:31][C:30]([O:29][CH2:28][CH:26]2[C:27]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:20]3[C:25]2=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:39])[CH:33]([CH3:35])[CH3:34])[N:9]=[C:8]([C:11]([CH3:13])([CH3:12])[CH3:14])[S:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 14353611HCID 14353611, compoundHCID 14804495HCID 14804495, compound

Product 1

HCID 68655055HCID 68655055, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred suspension of polyvinylpyridine (2.63 g, 25 mmol) in a solution of 5-tert-butyl-2,3-dihydro-[1,3,4]thiadiazole-2-carboxylic acid ethyl ester (36), (J. Med. Chem., 34, p. 439 (1991)), (2.16 g, 10 mmol) in dry toluene was treated with the dropwise addition of (1-chlorocarbonyl-2-methyl-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (4.76 g, 12.1 mmol) in 20 mL of anhydrous toluene. After stirring for 16 hours, the suspension was filtered and the filtrate was washed with saturated sodium bicarbonate solution. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and evaporated to give a yellow oil. Purification by flash chromatography eluting with 9/1 hexane/ethyl acetate gave 2.66 g (49% yield) of the title compound (37) as a clear, viscous oil. 1H NMR (500 MHz, CD3OD) δ 0.89 (d, 1.5H), 0.93 (d, 1.5H), 1.00 (d, 1.5H), 1.06 (d, 1.5H), 1.22 (t, 3H), 1.28 (s, 9H), 2.12-2.22 (m, 0.5H), 2.32-2.42 (m, 0.5H), 4.18-4.28 (m, 2H), 4.31-4.45 (m, 2H), 4.96-5.01 (m, 0.5H), 5.02-5.10 (m, 0.5H), 5.52 (d, 0.5H), 5.61 (d, 0.5H), 6.10 (s, 0.5H), 6.13 (s, 0.5H), 7.27-7.34 (m, 2H), 7.35-7.42 (m, 2H), 7.56-7.64 (m, 2H), 7.73-7.78 (m, 2H).

Workup

  1. filtrationthe suspension was filtered
  2. washthe filtrate was washed with saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto give a yellow oil
  8. customPurification by flash chromatography
  9. washeluting with 9/1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-843bc5824e9c4a6eb0e80fd1f6c44160
Source dataset
uspto-grants-2003_03
Patent number
US06531474B1

Reaction notes

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