4-Methylmorpholine → HCID 131715577, compound

HRID 579896Notes

Reaction equation

HRID 579896 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:15])[CH2:6][C@H:7]([OH:14])[C@H:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[NH2:9])[CH3:3].CN1CCOCC1.[C:23]([O:27][C:28]([NH:30][C@H:31]([C:36]([OH:38])=[O:37])[C@H:32]([CH2:34][CH3:35])[CH3:33])=[O:29])([CH3:26])([CH3:25])[CH3:24].ON1C2C=CC=CC=2N=N1.CC1C=CC(S([O-])(=O)=O)=CC=1.C[N+]1(CCN=C=NC2CCCCC2)CCOCC1>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:15])[CH2:6][C@H:7]([OH:14])[C@H:8]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH2:9])[CH3:3].[C:23]([O:27][C:28]([NH:30][C@H:31]([C:36]([OH:38])=[O:37])[C@H:32]([CH2:34][CH3:35])[CH3:33])=[O:29])([CH3:24])([CH3:26])[CH3:25]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 172201-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonateHCID 757711-HydroxybenzotriazoleHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 14557506HCID 14557506, compound

Product 1

HCID 131715577HCID 131715577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Statine ethyl ester hydrochloride (717 mg., 3 mmoles), N-methyl-morpholine (304 mg., 3 mmoles), N-(t-butyloxycarbonyl)-L-isoleucine 1/2H2O (865 mg., 3.6 mmoles), N-hydroxybenzotriazole (486 mg., 3.6 mmoles) and 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluene sulfonate (1.91 g., 80% pure, 3.6 mmoles) were added sequentially to 100 ml. of methylene chloride at 0° C. and the resulting solution allowed to stir for 19 hours at 20° C. The reaction mixture was then washed consecutively with 75 ml. of 5.5% aqueous HCl, 75 ml. of saturated aqueous NaHCO3 and 75 ml. of brine, and dried over anhydrous MgSO4. After filtration and evaporation, 1.39 g. of crude product was obtained as a foam (1NMR, CDCl3, 1.5 delta, 9H s [BOC]), which was used without further purification in the next step.

Workup

  1. customat 0° C.
  2. washThe reaction mixture was then washed consecutively with 75 ml
  3. dry with materialof brine, and dried over anhydrous MgSO4
  4. filtrationAfter filtration and evaporation, 1.39 g
  5. customof crude product was obtained as a foam (1NMR, CDCl3, 1.5 delta, 9H s [BOC]), which
  6. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-54ef418cd2e24e0ca90914ad064e66ee
Source dataset
uspto-grants-1988_06
Patent number
US04749687

Reaction notes

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