4-Methylmorpholine → N-[(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl carbamoyl]-methyl]-3(-2-methoxy-5-methylphenyl)-3-phenyl propionamide

HRID 2110552Notes

Reaction equation

HRID 2110552 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][C:12]([OH:14])=O.[NH2:21][CH2:22][C:23]([NH:25][CH:26]1[CH:31]2[CH:27]1[CH2:28][N:29]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:30]2)=[O:24].C(OC(C(N)C(O)=O)=O)(C)(C)C.C(N1CC2C(C2N)C1)C1C=CC=CC=1.CN1CCOCC1.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH2:32]([N:29]1[CH2:28][CH:27]2[CH:31]([CH:26]2[NH:25][C:23]([CH2:22][NH:21][C:12](=[O:14])[CH2:11][CH:10]([C:4]2[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:24])[CH2:30]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 757711-Hydroxybenzotriazole2×HCID 34683223-(2-Methoxy-5-methylphenyl)-3-phenylpropanoic acidHCID 14252312t-Butoxy carbonyl amino-acetic acidHCID 185069973-Benzyl-3-azabicyclo(3.1.0)hexan-6-amineHCID 688714602-amino-N-(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)-acetamide

Product 1

HCID 68921945N-[(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl carbamoyl]-methyl]-3(-2-methoxy-5-methylphenyl)-3-phenyl propionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound, 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid (209 mg, 0.77 mmole, 1 eq) and 2-amino-N-(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)-acetamide, 0.77 mmole, 1 eq (prepared by reacting t-butoxy carbonyl amino-acetic acid with 3-benzyl-3-azabicylo[3.1.0]hex-6-yl amine, which in turn, was prepared following the procedure of T. F. Braish et al., Synlett 1996, 1100) were dissolved in dimethylformamide (5 ml). The reaction mixture was cooled to 0° C. with subsequent addition of N-methyl morpholine (0.13 ml) and 1-hydroxy benzotriazole, HOBT (105 mg). The resulting mixture was diluted with water and extracted the organic compound with ethyl acetate. The solvent was removed under reduced pressure. The crude organic compound thus obtained was purified by column chromatography using 80% ethyl acetate in hexane. Yield=367 mg.

Workup

  1. customwas prepared
  2. extractionextracted the organic compound with ethyl acetate
  3. customThe solvent was removed under reduced pressure
  4. customThe crude organic compound thus obtained
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d5f0121f5aa44326b1eb6fc36fe5974e
Source dataset
uspto-grants-2009_04
Patent number
US07517905B2

Reaction notes

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