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Trifluoroacetic acid → (2s)-2-Benzyloxycarbonylamino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)-purin-9-yl)-propionic acid

HRID 351650
Notes
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Reaction equation

HRID 351650 reaction equation
C([O:5][C:6](=[O:45])[C@@H:7]([NH:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:33]=[CH:32][C:31]3[CH2:30][CH2:29][CH2:28][NH:27][C:26]=3[N:25]=2)[CH2:20][CH2:19]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:38]([O:37][C:35]([NH:34][C@@H:7]([CH2:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[N:18]1[CH2:19][CH2:20][CH:21]([C:24]2[CH:33]=[CH:32][C:31]3[CH2:30][CH2:29][CH2:28][NH:27][C:26]=3[N:25]=2)[CH2:22][CH2:23]1)[C:6]([OH:45])=[O:5])=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11422135(2s)-2-Benzyloxycarbonylamino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)-purin-9-yl)-propionic acid tert-butyl ester

Product 1

HCID 11444310(2s)-2-Benzyloxycarbonylamino-3-(6-(4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl)-purin-9-yl)-propionic acid

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

219 mg of the compound of step d) were dissolved in 12 ml of dichloromethane and 2 ml trifluoroacetic acid were added under stirring at ambient temperature. After 6 hours the reaction was complete. The solvents were removed in vacuo. The residue was mixed with toluene and this mixture was again evaporated. The resulting resin was triturated with diethylether. After filtration 210 mg of a faint yellow solid were isolated. MS (ES+): m/e=557.2 (M+H)+.

Workup

  1. customThe solvents were removed in vacuo
  2. additionThe residue was mixed with toluene
  3. customthis mixture was again evaporated
  4. customThe resulting resin was triturated with diethylether
  5. filtrationAfter filtration 210 mg of a faint yellow solid
  6. customwere isolated

Sources & evidence

ORD record
ord-ccf5ac98d312487189eb2dbeb221836f
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06743800B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes