Ethylmorpholine → HCID 11567002, compound

HRID 2302211Notes

Reaction equation

HRID 2302211 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH:45]1[CH2:53][CH2:52][CH2:51][C@H:46]1[C:47]([O:49][CH3:50])=[O:48].Cl.C(N1CCOCC1)C>CN(C)C=O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([N:45]1[CH2:53][CH2:52][CH2:51][C@H:46]1[C:47]([O:49][CH3:50])=[O:48])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 637610Boc-D-phenylalanineHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 11567002HCID 11567002, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of Boc-D-Phe-OH (5 g) in N,N-dimethyl formamide (200 ml) were successively added 1-hydroxy benzotriazole (4.29 g), dicyclohexyl carbodimide (4.29 g), H-Pro-OMe.HCl (3.1 g) and N-ethylmorpholine (3 ml). The mixture was stirred at 0° C. for 1 hour and then kept at room temperature for 2 days. The mixture was cooled to −20° C. and dicyclohexylurea was removed by filtration. The filtrate was evaporated to dryness. The residue was dissolved in ethyl acetate and washed successively with 5% sodium hydrogen carbonate, 0.1M hydrogen chloride-solution, saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel in heptane/ethyl acetate=6/4 (v/v) as eluent. The fractions containing Boc-D-Phe-Pro-OMe were pooled and evaporated. Yield: 1.5 g.

Workup

  1. waitkept at room temperature for 2 days
  2. temperatureThe mixture was cooled to −20° C.
  3. customdicyclohexylurea was removed by filtration
  4. customThe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed successively with 5% sodium hydrogen carbonate, 0.1M hydrogen chloride-solution, saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel in heptane/ethyl acetate=6/4 (v/v) as eluent
  10. additionThe fractions containing Boc-D-Phe-Pro-OMe
  11. customevaporated

Sources & evidence

ORD record
ord-7a93517c993e4b8c88e8cc8e51755cbe
Source dataset
uspto-grants-2002_08
Patent number
US06432921B1

Reaction notes

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