4-Methylmorpholine → HCID 131720134, compound

HRID 2258493Notes

Reaction equation

HRID 2258493 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3](Cl)=[O:4].Cl.[F:20][C:21]([F:33])([C:29]([F:32])([F:31])[F:30])[C:22]([CH:24]1[CH2:28][CH2:27][CH2:26][NH:25]1)=[O:23].CN1CCOCC1>C(Cl)Cl>[F:33][C:21]([F:20])([C:29]([F:30])([F:31])[F:32])[C:22]([CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:3]([CH:2]1[CH2:6][CH2:7][CH2:8][N:1]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=[O:4])=[O:23]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1103285461350-60-5HCID 22922469HCID 22922469, compound

Product 1

HCID 131720134HCID 131720134, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methylene chloride (10 ml) was added to CBZ-L-Pro-Cl which was then reacted under argon with a suspension of 2-(2,2,3,3,3-pentafluoro-1-oxopropyl)pyrrolidine hydrochloride (compound from Example IC; 2.49 mmol) and N-methylmorpholine (0.54 ml; 4.98 mmol) dissolved in methylene chloride (7 ml). After 2.5 hours the reaction was concentrated and brought up in methylene chloride (1 ml) and the product purified by flash chromatography on silica gel column eluting with ethyl acetate/hexane (50:50). Product fractions were collected and concentrated to give the desired product (0.52 g) as a colorless oil.

Workup

  1. concentrationAfter 2.5 hours the reaction was concentrated
  2. customthe product purified by flash chromatography on silica gel column
  3. washeluting with ethyl acetate/hexane (50:50)
  4. customProduct fractions were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a3ee2c108d44fbe8ba9cc7336cd3aa8
Source dataset
uspto-grants-1997_08
Patent number
US05661167

Reaction notes

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