4-[2-(Pyrimidin-2-ylamino)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine alanine trifluoroacetate → 2-Benzenesulfonylamino-3-{4-[2-(1,4,5,6-tetrahydro-pyrimidin-2-ylamino)-ethoxy]-benzoylamino}-propionic acid

HRID 1599927Notes

Reaction equation

HRID 1599927 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[NH2:8][C@H](C(O)=[O:12])C.[N:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[NH:20][CH2:21][CH2:22][O:23][C:24]1[CH:47]=[CH:46][C:27]([C:28]([NH:30][CH2:31][C@H:32]([NH:36][S:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=[O:39])=[O:38])[C:33]([OH:35])=[O:34])=[O:29])=[CH:26][CH:25]=1>C(O)(=O)C.Cl.[Pd]>[CH3:2][CH2:3][OH:4].[NH4+:8].[OH-:12].[OH2:23].[N:14]1[CH2:19][CH2:18][CH2:17][NH:16][C:15]=1[NH:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]([NH:30][CH2:31][C@H:32]([NH:36][S:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=[O:39])=[O:38])[C:33]([OH:35])=[O:34])=[O:29])=[CH:46][CH:47]=1

Participants

6

Reactant 1

HCID 867524424-[2-(Pyrimidin-2-ylamino)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine alanine trifluoroacetate

Product 2

HCID 99134292-Benzenesulfonylamino-3-{4-[2-(1,4,5,6-tetrahydro-pyrimidin-2-ylamino)-ethoxy]-benzoylamino}-propionic acidHCID 86596525Ethanol ammonium hydroxide water

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

Pyrimidine 19-8 (1.05 g, 1.75 mmol) was dissolved in a mixture of acetic acid (50 mL) and conc HCl (4.5 mL). After addition of 10% Pd/C (450 mg) the mixture was shaken on a Parr hydrogenator under 45 psi H2 pressure for 2 h. The reaction mixture was filtered, concentrated, azeotroped with toluene, and purified by flash chromatography (silica 20:1:1 then 8:1:1 EtOH/NH4OH/H2O) providing 19-9 as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customazeotroped with toluene
  4. custompurified by flash chromatography (silica 20:1:1

Sources & evidence

ORD record
ord-83b5c3465cec424d863679ced3cc1535
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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