4-Methylmorpholine → HCID 131720626, compound

HRID 1599716Notes

Reaction equation

HRID 1599716 reaction equation
[C:1]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:22]1[CH:23]=[CH:24][C:25]2[N:30](O)[N:29]=[N:28][C:26]=2C=1.CC[N:34]=C=NCCCN(C)C.CN1CCOCC1.OS([O-])(=O)=O.[K+]>CN(C=O)C.C(OCC)(=O)C>[N:28]([CH2:26][CH:25]1[CH2:24][CH2:23][CH2:22][N:30]1[C:19](=[O:21])[CH:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[N+:29]=[N-:34]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 516920Potassium bisulfate

Product 1

HCID 131720626HCID 131720626, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Example 1a Part A compound (2.13 g, 9.4 mmol) was dissolved in dichloromethane (5 mL) and trifluoroacetic acid (7 mL) and stirred at RT 3 hours. The TFA and dichloromethane were removed by distillation under reduced pressure and by coevaporation with toluene to give the amine as a TFA salt. This and N-BOC-O-benzyl-L-serine (2.95 g, 10 mmol) were dissolved in DMF (50 mL). HOBT (1.35 g, 10 mmol), WSC (1.91 g, 10 mmol) and NMM (3.3 mL, 30 mmol) were added. The reaction was stirred for 8 h at room temperature, diluted with ethyl acetate (50 mL) and satd. KHSO4 solution (30 mL). The layers were separated and the aqueous layer was reextracted with ethyl acetate (50 mL). The combined organic layers were washed with saturated sodium bicarbonate solution (30 mL)) and 10% lithium chloride solution (30 mL). The ethyl acetate layer was dried over magnesium sulfate and concentrated in vacuo to provide title compound (3.87 g, 100%) as an oil which was used without further purification.

Workup

  1. customThe layers were separated
  2. washThe combined organic layers were washed with saturated sodium bicarbonate solution (30 mL)) and 10% lithium chloride solution (30 mL)
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a170f9cb3a64d0394bdb951b1e3baa0
Source dataset
uspto-grants-1998_04
Patent number
US05741792

Reaction notes

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