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

HRID 583675Notes

Reaction equation

HRID 583675 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[N:8]1[CH:13]=[CH:12][CH:11]=[N:10][C:9]=1[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:41]=[CH:40][C:21]([C:22]([NH:24][CH2:25][C@H:26]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:27]([OH:29])=[O:28])=[O:23])=[CH:20][CH:19]=1>C(O)(=O)C.Cl.[Pd]>[CH3:2][CH2:3][OH:4].[NH4+:8].[OH-:17].[OH2:4].[N:8]1[CH2:13][CH2:12][CH2:11][NH:10][C:9]=1[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:24][CH2:25][C@H:26]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:27]([OH:29])=[O:28])=[O:23])=[CH:40][CH:41]=1

Participants

6

Reactant 1

HCID 867543364-[2-(Pyrimidin-2-ylamino)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-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-1552c97adddd414197a98300bcc62fe7
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

Loading…