tert-Butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionate → (2S)-2-Benzyloxycarbonylamino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2ylcarbamoyl)ethyl)benzoylamino)propionic Acid

HRID 984033Notes

Reaction equation

HRID 984033 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][NH:21][C:22](=[O:40])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](=[O:39])[NH:32][C:33]2[NH:34][CH2:35][CH2:36][CH2:37][N:38]=2)=[CH:25][CH:24]=1)[C:13]([O:15]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][NH:21][C:22](=[O:40])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31](=[O:39])[NH:32][C:33]2[NH:38][CH2:37][CH2:36][CH2:35][N:34]=2)=[CH:25][CH:24]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 15512204tert-Butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

190 mg (0.34 mmol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-(1,4,5,6tetrahydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionate (step d) were dissolved in 5 ml of 95% trifluoroacetic acid and the mixture was stirred at room temperature for 1 h. The trifluoroacetic acid was distilled off in vacuo and the mixture was co-evaporated with toluene. The residue was dissolved in glacial acetic acid, and the solution was diluted with water and freeze-dried.

Workup

  1. distillationThe trifluoroacetic acid was distilled off in vacuo
  2. dissolutionThe residue was dissolved in glacial acetic acid
  3. additionthe solution was diluted with water
  4. customfreeze-dried

Sources & evidence

ORD record
ord-7d2e76f689194d74b0310abe69a11f52
Source dataset
uspto-grants-2005_03
Patent number
US06867213B2

Reaction notes

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