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

HRID 1394011Notes

Reaction equation

HRID 1394011 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.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

6

Reactant 3

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

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-tetra-hydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionic acid (Example 3e) were dissolved in 15 ml of dioxane, treated with 0.012 ml of glacial acetic acid and hydrogenated at RT and 1 bar H2 over Pd/C (5%). After 2 h, 15 ml of methanol were added and the mixture was hydrogenated at RT and 1 bar H2 for a further 5 h. It was filtered and the solvent was evaporated in vacuo. Yield: 67.4 mg (93%). MS: ES+, m/e=362.2 (M+H+, 30%); 173.0 (100).

Workup

  1. customwas hydrogenated at RT
  2. wait1 bar H2 for a further 5 h
  3. filtrationIt was filtered
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b881d24481c94ec18b0f0f4d3fe62bd8
Source dataset
uspto-grants-2008_03
Patent number
US07348333B2

Reaction notes

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