4-Methylmorpholine → HCID 15896003, compound

HRID 2184782Notes

Reaction equation

HRID 2184782 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][C@H:11]([C:15]([OH:17])=O)[N:10]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.C(N=C=NCCCN(C)C)C.Cl.[CH2:58]([O:65][NH2:66])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>CN(C)C=O.O>[CH2:58]([O:65][NH:66][C:15]([C@H:11]1[CH2:12][C:13](=[O:14])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][N:10]1[S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:20])=[O:19])=[O:17])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 15896002HCID 15896002, compound

Product 1

HCID 15896003HCID 15896003, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Benzyl-3-[(4-methoxyphenyl)sulfonyl]-6-oxo-hexahydro-pyrimidine-4(R)-carboxylic acid (206 mg, 0.5 mmol) is dissolved in N,N-dimethylformamide (20 mL) and is cooled to 0° C. To this is added 1-hydroxybenzotriazole (203 mg, 1.5 mmol), 4-methylmorpholine (0.16 mL, 1.5 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (117 mg, 0.61 mmol) followed, after 20 minutes, with O-benzylhydroxylamine hydrochloride (89 mg, 0.56 mmol). The reaction is stirred for 4 hours at room temperature, water (50 mL) is added and the product is extracted with ethyl acetate (3×). The combined organic phases are washed with water (2×), dried (Na2SO4) and concentrated under reduced pressure to give N-benzyloxy 1-benzyl-3-[(4-methoxyphenyl)sulfonyl]-6-oxo-hexahydro-pyrimidine-4(R)-carboxamide.

Workup

  1. extractionthe product is extracted with ethyl acetate (3×)
  2. washThe combined organic phases are washed with water (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d9aff40a98bc4a6a82e0962e678f7de5
Source dataset
uspto-grants-2002_06
Patent number
US06399598B1

Reaction notes

Loading…