Ethylmorpholine → HCID 23317401, compound

HRID 1982163Notes

Reaction equation

HRID 1982163 reaction equation
CC(C[S:7]C(=O)C)C(O)=O.Cl.C[O:13][C:14]([CH:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17]1)=[O:15].ON1C2C=C[CH:34]=[CH:35][C:30]=2N=N1.C(N1C[CH2:42][O:41]CC1)C.C1(N=C=NC2CCCCC2)CCCCC1>CC(N(C)C)=O>[SH:7][CH:25]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:42](=[O:41])[CH:35]([CH3:34])[CH3:30])[CH:16]1[C:14]([OH:13])=[O:15]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1180733-(Acetylthio)-2-methylpropanoic acidHCID 2747398Methyl 1,2,3,4-tetrahydroquinoline-2-carboxylate Hydrochloride

Product 1

HCID 23317401HCID 23317401, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.63 g of 2-methyl-3-acetylmercaptopropionic acid and 2.3 g of 1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester hydrochloride, prepared as described in Chem. Ber. 61, page 2377 (1928), are dissolved under nitrogen in 20 ml of dimethyl acetamide. 1.35 g of 1-hydroxy-benzotriazole, 1.28 ml of N-ethylmorpholine and 2.2 g of dicyclohexyl carbodiimide are successively added and the whole is stirred for 4 hours at room temperature. The reaction mixture is then filtered and the solvent is distilled off from the filtrate in vacuo. The residue is dissolved in 30 ml of methanol. The solution is stirred and 10 ml of 4N NaOH are added drop by drop and under nitrogen. 10 minutes after termination of the addition, 10 ml of 4N HCl are added, whereupon the mixture is evaporated to dryness in vacuo. After distillation of the solvent, the reaction product is purified by chromatography on 130 g of SiO2 in a system of chloroform/isopropanol/acetic acid (50:10:3). Yield 2.3 g. Elemental analysis and NMR spectrum correct.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. distillationthe solvent is distilled off from the filtrate in vacuo
  3. dissolutionThe residue is dissolved in 30 ml of methanol
  4. stirringThe solution is stirred
  5. addition10 ml of 4N NaOH are added drop by drop
  6. addition10 minutes after termination of the addition, 10 ml of 4N HCl
  7. additionare added, whereupon the mixture
  8. customis evaporated to dryness in vacuo
  9. distillationAfter distillation of the solvent
  10. customthe reaction product is purified by chromatography on 130 g of SiO2 in a system of chloroform/isopropanol/acetic acid (50:10:3)

Sources & evidence

ORD record
ord-941dbf1c76774d96b4d45d52e968c73f
Source dataset
uspto-grants-1986_06
Patent number
US04595675

Reaction notes

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