4-Methylmorpholine → HCID 54304839, compound

HRID 1829597Notes

Reaction equation

HRID 1829597 reaction equation
[NH2:1][C@@H:2]([C:12]([O:14][CH3:15])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[O:17]=[C:18]1[N:24]([CH2:25][CH2:26][C:27](O)=[O:28])[C:23]2[CH:30]=[CH:31][CH:32]=[CH:33][C:22]=2[S:21][CH2:20][CH2:19]1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])O.[Na+]>C(Cl)CCl.CN(C=O)C>[CH3:15][O:14][C:12](=[O:13])[CH:2]([NH:1][C:27](=[O:28])[CH2:26][CH2:25][N:24]1[C:23]2[CH:30]=[CH:31][CH:32]=[CH:33][C:22]=2[S:21][CH2:20][CH2:19][C:18]1=[O:17])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 10988739HCID 10988739, compoundHCID 119088438HCID 119088438, compound

Product 1

HCID 54304839HCID 54304839, compoundYield 111.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To DMF(2 ml) solution of D-Ser(Bzl)-OMe hydrochloride(141 mg) and 3-(4-oxo-2,3-dihydro-1,5-benzothiazepin-5-yl)-propionic acid(138 mg),N-methyl morpholine(61 mg), HOBt(92 mg) and EDC(125 mg) were added under cooling on ice-water and then stirring is continued at room temperature overnight. After reaction, reaction mixture was poured into saturated sodium hydrogen carbonate solution(20 ml) and then extracted with ethyl acetate. Ethyl acetate layer was dried on anhydrous sodium sulfate and then evaporated to dryness. Title compound(270 mg) was isolated by using silica gel chromatography(CHCl3:MeOH=100:1).

Workup

  1. temperatureunder cooling on ice-water
  2. customAfter reaction, reaction mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialEthyl acetate layer was dried on anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8b9e8096af5e4dc3987dd1d6a0bff445
Source dataset
uspto-grants-2006_06
Patent number
US07064121B2

Reaction notes

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