Triethylamine → HCID 15589902, compound

HRID 371360Notes

Reaction equation

HRID 371360 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:11])[C@@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1)[CH3:3].C(N(CC)CC)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[S:28])=[CH:22][C:21]=1[C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30]>C1C=CC=CC=1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([N:7]2[CH2:8][CH2:9][CH2:10][CH:6]2[C:5]([O:4][CH2:2][CH3:3])=[O:11])=[S:28])=[CH:22][C:21]=1[C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11679912Ethyl L-prolinate hydrochlorideHCID 20272617HCID 20272617, compound

Product 1

HCID 15589902HCID 15589902, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.8 g (0.01 mol) of proline ethyl ester hydrochloride and 1.0 g of triethylamine were added dropwise to 30 ml of benzene and 2.6 g (0.01 mol) of 4-chloro-3-isopropoxycarbonylphenyl isothiocyanate were added thereto. The mixture was stirred at room temperature for an hour, washed with water, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by means of silica gel column chromatography to give 2.5 g (yield 63%) of the desired product as a yellow glassy substance.

Workup

  1. additionwere added
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-65d9f3ba19e84f7d80835e7d75255b9f
Source dataset
uspto-grants-1985_07
Patent number
US04531964

Reaction notes

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