(2S)-2-benzyloxycarbonylamino-3-{9-[3-(1,4,5,6-tetrahydro-pyrimidin-2-ylcarbamoyl)-propyl]-9H-purin-6-ylamino}-propionic acid tert-butyl ester → (2S)-2-Benzyloxycarbonylamino-3-{9-[3-(1,4,5,6-tetrahydro-pyrimidin-2-ylcarbamoyl)-propyl]-9H-purin-6-ylamino}-propionic Acid

HRID 854249Notes

Reaction equation

HRID 854249 reaction equation
C([O:5][C:6](=[O:42])[C@@H:7]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH2:8][NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH2:19][CH2:20][CH2:21][C:22](=[O:30])[NH:23][C:24]1[NH:25][CH2:26][CH2:27][CH2:28][N:29]=1)(C)(C)C>FC(F)(F)C(O)=O.O>[CH2:35]([O:34][C:32]([NH:31][C@@H:7]([CH2:8][NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH2:19][CH2:20][CH2:21][C:22](=[O:30])[NH:23][C:24]1[NH:25][CH2:26][CH2:27][CH2:28][N:29]=1)[C:6]([OH:42])=[O:5])=[O:33])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 1

HCID 15547266(2S)-2-benzyloxycarbonylamino-3-{9-[3-(1,4,5,6-tetrahydro-pyrimidin-2-ylcarbamoyl)-propyl]-9H-purin-6-ylamino}-propionic acid tert-butyl ester

Product 1

HCID 15547257(2S)-2-Benzyloxycarbonylamino-3-{9-[3-(1,4,5,6-tetrahydro-pyrimidin-2-ylcarbamoyl)-propyl]-9H-purin-6-ylamino}-propionic Acid

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

70 mg (Q.12 mmol) of (2S)-2-benzyloxycarbonylamino-3-{9-[3-(1,4,5,6-tetrahydro-pyrimidin-2-ylcarbamoyl)-propyl]-9H-purin-6-ylamino}-propionic acid tert-butyl ester was dissolved in 3 ml of trifluoroacetic acid/water (95/5). The solution was stirred at room temperature for 3 hours. The solvent was removed in vacuo and toluene was added to the residue and then removed in vacuo. The residue was dissolved in acetonitrile/water 1/1 and lyophilized. Yield: 51 mg (trifluoroacetate salt).

Workup

  1. customThe solvent was removed in vacuo and toluene
  2. additionwas added to the residue
  3. customremoved in vacuo
  4. dissolutionThe residue was dissolved in acetonitrile/water 1/1

Sources & evidence

ORD record
ord-35830b427dad41b291ce0bbbf227bea8
Source dataset
uspto-grants-2007_08
Patent number
US07259159B2

Reaction notes

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