3-{[(Tert-butoxy)carbonyl]amino}-3-phenylpropanoic acid → HCID 178454421, compound

HRID 538046Notes

Reaction equation

HRID 538046 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([C:28]([N:30]2[CH2:35][CH2:34][N:33]([C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])[CH2:32][CH2:31]2)=[O:29])[CH2:24][CH2:23]1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][C:11](=[O:13])[NH:20][CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([C:28]([N:30]2[CH2:35][CH2:34][N:33]([C:36](=[O:40])[CH:37]([CH3:38])[CH3:39])[CH2:32][CH2:31]2)=[O:29])[CH2:24][CH2:23]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 27568153-{[(Tert-butoxy)carbonyl]amino}-3-phenylpropanoic acidHCID 178454419HCID 178454419, compound

Product 1

HCID 178454421HCID 178454421, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a solution of 3-tert-Butoxycarbonylamino-3-phenyl-propionic acid (0.43 g, 1.63 mmol) in DCM (20 mL), 1,1-carbonyldiimidazole (0.24 g, 1.48 mmol) was added and the reaction was stirred for 2 hours at room temperature. Then 1-[trans-4-(4-Aminomethyl-cyclohexanecarbonyl)-piperazin-1-yl]-2-methyl-propan-1-one (0.40 g, 1.36 mmol) was added and the mixture was left for 18 hours at room temperature. The mixture was diluted with 10 mL of 0.4 M Na2CO3, the organic phase was collected and the solvent removed under reduced pressure. The residue was washed with 20 mL solution of NH4Cl and the precipitate filtered. The titled compound was isolated as a white solid (0.65 g, 88% yield).

Workup

  1. waitthe mixture was left for 18 hours at room temperature
  2. customthe organic phase was collected
  3. customthe solvent removed under reduced pressure
  4. washThe residue was washed with 20 mL solution of NH4Cl
  5. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-3a86b4f51c294b5294d42f2432e0c24c
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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