4-Methylmorpholine → HCID 18517998, compound

HRID 1368906Notes

Reaction equation

HRID 1368906 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:5].[CH3:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])[CH:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[CH3:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH2:30][CH2:31][CH2:32][C:33]([NH:2][CH2:3][C:4]([NH:6][CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:5])=[O:34])[CH:24]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 18517990HCID 18517990, compoundHCID 18518092HCID 18518092, compound

Product 1

HCID 18517998HCID 18517998, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

360 mg of methyl 3-(2-aminoacetylamino)-3-(2-nitrophenyl)propionate hydrochloride are dissolved in 35 ml of DMF, and 190 mg of 4-(4-methylpyridin-2-ylamino)butyric acid are added. After cooling the reaction mixture to 0°, 450 mg of TBTU and 63 mg of HOBt are added. It is neutralized with 0.15 ml of N-methylmorpholine and stirred at room temperature overnight. The solvent is distilled off, and the residue is mixed with 30 ml of ethyl acetate and washed with half-concentrated bicarbonate solution and saturated brine and worked up further as usual. Methyl 3-{2-[4-(4-methylpyridin-2-ylamino)butyrylamino]acetylamino}-3-(2-nitrophenyl)propionate is obtained.

Workup

  1. temperatureAfter cooling the reaction mixture to 0°
  2. distillationThe solvent is distilled off
  3. additionthe residue is mixed with 30 ml of ethyl acetate
  4. washwashed with half-concentrated bicarbonate solution and saturated brine

Sources & evidence

ORD record
ord-54e34fbedc3743798bacc893117acbd7
Source dataset
uspto-grants-2003_06
Patent number
US06576637B1

Reaction notes

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