Acetic Acid → (2S)-2-Amino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)benzoylamino)propionic acid

HRID 984034Notes

Reaction equation

HRID 984034 reaction equation
C(OC([NH:11][C@@H:12]([CH2:16][NH:17][C:18](=[O:36])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](=[O:35])[NH:28][C:29]2[NH:30][CH2:31][CH2:32][CH2:33][N:34]=2)=[CH:21][CH:20]=1)[C:13]([OH:15])=[O:14])=O)C1C=CC=CC=1.C(O)(=O)C.[H][H].CO>O1CCOCC1.[Pd]>[NH2:11][C@@H:12]([CH2:16][NH:17][C:18](=[O:36])[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][C:27](=[O:35])[NH:28][C:29]2[NH:34][CH2:33][CH2:32][CH2:31][N:30]=2)=[CH:23][CH:24]=1)[C:13]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 15512205(2S)-2-Benzyloxycarbonylamino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2ylcarbamoyl)ethyl)benzoylamino)propionic AcidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15512206(2S)-2-Amino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)benzoylamino)propionic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

100 mg (0.2 mmol) of (2S)-2-benzyloxycarbonylamino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionic acid (step e) were dissolved in 15 ml of dioxane, treated with 0.012 ml of glacial acetic acid and hydrogenated at room temperature under 1 bar of hydrogen over palladium/charcoal (5%). After 2 h, 15 ml of methanol were added and the mixture was hydrogenated at room temperature under 1 bar of hydrogen for further 5 h. It was then filtered and the solvent was evaporated in vacuo. Yield: 67.4 mg (93%).

Workup

  1. filtrationIt was then filtered
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1bb48c5d38014bfe83c42cd4ae3f26e1
Source dataset
uspto-grants-2005_03
Patent number
US06867213B2

Reaction notes

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