Triethylamine → HCID 178442817, compound

HRID 846193Notes

Reaction equation

HRID 846193 reaction equation
Cl[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:3]([O:5][CH3:6])=[O:4].[SH:25][CH2:26][CH2:27][C:28]1[NH:32][N:31]=[N:30][N:29]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:2]([S:25][CH2:26][CH2:27][C:28]1[NH:32][N:31]=[N:30][N:29]=1)[C:3]([O:5][CH3:6])=[O:4])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15617386HCID 15617386, compoundHCID 178528007HCID 178528007, compound

Product 1

HCID 178442817HCID 178442817, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-chloro-2-(2-dodecyl phenyl)acetate (0.615 g, 1.75 mmol), 5-(2-mercaptoethyl)-tetrazole (0.227 g, 1.75 mmol), and triethylamine (0.48 ml), 3.5 mmol) in 20 ml of methylene chloride was stirred 18 hours at 22° and the solvent was evaporated. The residue taken up in diethyl ether, washed with 1 N hydrochloric acid, dried and the solvent removed. The residue was chromatographed over a silica gel column. Impurities were eluted with ethyl acetate/hexane (1:3), and the product was eluted with methanol/ethyl acetate (1:19). Evaporation of the solvents from these fractions gave the desired product, 0.570 g (73%).

Workup

  1. customthe solvent was evaporated
  2. washwashed with 1 N hydrochloric acid
  3. customdried
  4. customthe solvent removed
  5. customThe residue was chromatographed over a silica gel column
  6. washImpurities were eluted with ethyl acetate/hexane (1:3)
  7. washthe product was eluted with methanol/ethyl acetate (1:19)
  8. customEvaporation of the solvents from these fractions

Sources & evidence

ORD record
ord-5dd6e1168ff648c0b27d8b2863c920f0
Source dataset
uspto-grants-1992_08
Patent number
US05135938

Reaction notes

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