4-Methylmorpholine → HCID 70000535, compound

HRID 279716Notes

Reaction equation

HRID 279716 reaction equation
[C:1]1([CH3:29])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:28][CH2:27][CH2:26][C@H:11]2[C:12]([NH:14][C@H:15]([C:23](O)=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[CH2:64]([O:66][C:67](=[O:71])[CH2:68][CH2:69][NH2:70])[CH3:65]>CN(C=O)C>[CH2:64]([O:66][C:67](=[O:71])[CH2:68][CH2:69][NH:70][C:23](=[O:24])[CH:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:14][C:12](=[O:13])[C@@H:11]1[CH2:26][CH2:27][CH2:28][N:10]1[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:29])=[CH:2][CH:3]=1)(=[O:8])=[O:9])[CH3:65]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 419889Ethyl 3-aminopropanoateHCID 9931728HCID 9931728, compound

Product 1

HCID 70000535HCID 70000535, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-(toluene-4-sulfonyl)-L-prolyl-L-phenylalanine (˜2 eq.) in DMF was added BOP (˜2.1 eq.) and NMM (˜4 eq.), and the reaction was stirred at room temperature for about 45 minutes. β-alanine ethyl ester (˜2 eq.) was added and the reaction stirred for about 16 hours at room temperature. The reaction mixture was extracted with water and diethyl ether. The combined organic solution was then washed with 0.2 N HCl, sat. NaHCO3 and sat. NaCl solutions. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (50% EtOAc/Hexane, Rf=0.18) to yield the title compound as a colorless oil, which was determined to be a mixture of diastereomers by NMR.

Workup

  1. stirringthe reaction stirred for about 16 hours at room temperature
  2. extractionThe reaction mixture was extracted with water and diethyl ether
  3. washThe combined organic solution was then washed with 0.2 N HCl, sat. NaHCO3 and sat. NaCl solutions
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (50% EtOAc/Hexane, Rf=0.18)

Sources & evidence

ORD record
ord-22cf4106182e4a2c9a1063a8e32b1ac7
Source dataset
uspto-grants-2002_03
Patent number
US06362341B1

Reaction notes

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