Diisopropylethylamine → HCID 18659860, compound

HRID 1291763Notes

Reaction equation

HRID 1291763 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7](Cl)=[O:8])[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:30]([O:37][C:38](=[O:44])[C@H:39]([CH:41]([CH3:43])[CH3:42])[NH2:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.C(OCC)(=O)C>[CH2:30]([O:37][C:38](=[O:44])[C@H:39]([CH:41]([CH3:42])[CH3:43])[NH:40][C:7]([N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)=[O:8])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 11567066O-benzyl-L-valine toluene-p-sulphonate

Product 1

HCID 18659860HCID 18659860, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.8 ml (8.1 mmol) of (morpholinocarbonyl)chloride (preparation: J. Med. Chem. 31, 2277 (1988)) and 4.1 ml (24.1 mmol) of N-ethyldiisopropylamine are added to a solution of 4 g (10.5 mmol) of (L)-valine-benzyl ester 4-toluenesulfonate in 56 ml of methylene chloride and the mixture is stirred at RT for 24 h. The reaction mixture is diluted with ethyl acetate and washed in succession with 1N hydrochloric acid, water, saturated sodium hydrogen carbonate solution and brine. The organic phase is dried over sodium sulfate and concentrated by evaporation. Chromatography on silica gel with ethyl acetate yields N-morpholinocarbonyl-(L)-valine-benzyl ester in the form of a colourless oil. The ester is directly further used in a).

Workup

  1. washwashed in succession with 1N hydrochloric acid, water, saturated sodium hydrogen carbonate solution and brine
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a0d1886de4574dcb86e8626afbc6454f
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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