4-Methylmorpholine → HCID 12797531, compound

HRID 1413125Notes

Reaction equation

HRID 1413125 reaction equation
[C:1]([O:5][C:6](=[O:23])[C@H:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1)([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.[C:31]([S:34][CH2:35][CH:36]([CH3:40])[C:37](Cl)=[O:38])(=[O:33])[CH3:32]>ClCCl>[C:1]([O:5][C:6](=[O:23])[C@H:7]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:37](=[O:38])[CH:36]([CH3:40])[CH2:35][S:34][C:31](=[O:33])[CH3:32])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 11723418HCID 11723418, compound

Product 1

HCID 12797531HCID 12797531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of L-prolyl-L-phenylalanine tert-butyl ester (1.0 g) [prepared by the method described in Ann. Chem. 680, 132-141 (1964)] in dichloromethane at about -30° C. were added N-methylmorpholine (0.32 g) and then dropwise 3-acetylthio-2-methylpropanoyl chloride (0.57 g). The mixture was stirred at the same temperature for 30 minutes and then at room temperature for one hour. The reaction mixture was washed successively with 4% sodium bicarbonate, water, 10% citric acid, and water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica gel with chloroform to give 1-(3-acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine tert-butyl ester.

Workup

  1. waitat room temperature for one hour
  2. washThe reaction mixture was washed successively with 4% sodium bicarbonate, water, 10% citric acid, and water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel with chloroform

Sources & evidence

ORD record
ord-dc150ba130c942a8b683a375167e566a
Source dataset
uspto-grants-1981_02
Patent number
US04248883

Reaction notes

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