Trifluoroacetic acid → benzylguanine N-Fmoc-piperidine

HRID 570992Notes

Reaction equation

HRID 570992 reaction equation
NC[C:3]1[C:8]([CH2:9][NH:10][C:11]2[NH:12][C:13](=[O:20])[C:14]3[NH:15][CH:16]=[N:17][C:18]=3[N:19]=2)=[CH:7][CH:6]=[CH:5][CH:4]=1.C([CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH:34]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]3[C:35]2=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:31])[CH2:26][CH2:25]1)(O)=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.FC(F)(F)C(O)=O>CN(C)C=O.O.C(#N)C>[CH2:9]([NH:10][C:11]1[NH:12][C:13](=[O:20])[C:14]2[NH:15][CH:16]=[N:17][C:18]=2[N:19]=1)[C:8]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:30]([N:27]1[CH2:28][CH2:29][CH2:24][CH2:25][CH2:26]1)([O:32][CH2:33][CH:34]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27364901-{[(9H-Fluoren-9-yl)methoxy]carbonyl}piperidine-4-carboxylic acidHCID 1363862616-Aminomethylbenzylguanine

Product 1

HCID 136386262benzylguanine N-Fmoc-piperidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Weighed into a 50 ml round-bottomed flask were 48.1 mg (178 μmol) of 6-aminomethylbenzylguanine which was partially dissolved in 10 ml of anhydrous dimethylformamide. 62.5 mg (178 μmol) of 4-carboxy-N-Fmoc-piperidine and 57.1 mg (178 μmol) of TBTU were added. The reaction mixture was left stirring for two hours. The reaction was monitored by HPLC on a Merck Lichrospher RP °18, 5 μm, 125×4.6 column with a gradient of acetonitrile in water containing 0.2% of trifluoroacetic acid.

Workup

  1. customWeighed into a 50 ml round-bottomed flask were
  2. waitThe reaction mixture was left

Sources & evidence

ORD record
ord-bceedb4d589c41efb05e7185ba13d1b3
Source dataset
uspto-grants-2015_05
Patent number
US09024022B2

Reaction notes

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