(2S)-3-{4-[3-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-propoxy]-phenyl}-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester → (2S)-3-{4-[3-(1,4,5,6-Tetrahydropyrimidin-2-ylcarbamoyl)-propoxy]-phenyl}-2-(toluene4-sulfonylamino)-propionic acid

HRID 1250872Notes

Reaction equation

HRID 1250872 reaction equation
C([O:5][C:6](=[O:39])[C@@H:7]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]2[NH:22][CH2:23][CH2:24][CH2:25][N:26]=2)=[CH:11][CH:10]=1)(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O.O>[NH:26]1[CH2:25][CH2:24][CH2:23][N:22]=[C:21]1[NH:20][C:19]([CH2:18][CH2:17][CH2:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][C@H:7]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:6]([OH:39])=[O:5])=[CH:14][CH:13]=1)=[O:27]

Participants

4

Reactant 1

HCID 57120024(2S)-3-{4-[3-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-propoxy]-phenyl}-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester

Product 1

HCID 9913985(2S)-3-{4-[3-(1,4,5,6-Tetrahydropyrimidin-2-ylcarbamoyl)-propoxy]-phenyl}-2-(toluene4-sulfonylamino)-propionic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

240 mg of (2S)-3-{4-[3-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-propoxy]-phenyl}-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester were dissolved in 5 ml of methylene chloride and 1.6 ml of trifluoroacetic acid/water (95/5). The mixture was stirred for 2 hours at ambient temperature. The solvents were removed in vacuo. The residue was triturated with diethyl ether, filtered and dried in vacuo. Yield 196 mg. MS (ES+): m/e=503.1 (M+H)+.

Workup

  1. customThe solvents were removed in vacuo
  2. customThe residue was triturated with diethyl ether
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f84b3c1c20f54bd690ced4c2fbde5efa
Source dataset
uspto-grants-2002_01
Patent number
US06340679B1

Reaction notes

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