Piperidine → N5-(4-(2,2-bis(diallylphosphoryl)ethyl)phenyl)-L-glutamine

HRID 39274Notes

Reaction equation

HRID 39274 reaction equation
C1C2C(COC([NH:18][C@H:19]([C:49]([OH:51])=[O:50])[CH2:20][CH2:21][C:22](=[O:48])[NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([P:40]([CH2:45][CH:46]=[CH2:47])([CH2:42][CH:43]=[CH2:44])=[O:41])[P:32]([CH2:37][CH:38]=[CH2:39])([CH2:34][CH:35]=[CH2:36])=[O:33])=[CH:26][CH:25]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[CH2:37]([P:32]([CH:31]([P:40]([CH2:42][CH:43]=[CH2:44])([CH2:45][CH:46]=[CH2:47])=[O:41])[CH2:30][C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:22](=[O:48])[CH2:21][CH2:20][C@@H:19]([C:49]([OH:51])=[O:50])[NH2:18])=[CH:25][CH:26]=1)([CH2:34][CH:35]=[CH2:36])=[O:33])[CH:38]=[CH2:39]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86762032N2-(9-fluorenylmethoxycarbonyl)-N5-(4-(2,2-bis(diallylphosphoryl)ethyl)phenyl)-L-glutamine

Product 1

HCID 86762031N5-(4-(2,2-bis(diallylphosphoryl)ethyl)phenyl)-L-glutamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Fmoc-protected compound 105 (431 mg, 0.51 mmol) was treated with a 5% v/v solution of piperidine in DMF (2.5 mL). After stirring for 2.5 h, the reaction mixture was concentrated to dryness and purified by silica gel chromatography on a Biotage™ flash chromatography system using a gradient of 0-10% methanol in CH2Cl2. Compound 106 was obtained as a colorless oil (246 mg, 77%). 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.82-1.91 (m, 1H), 2.16-2.24 (m, 1H), 2.45-2.60 (m, 2H), 2.71 (tt, J=23.9, 6.2 Hz, 1H), 3.24 (dt, J=16.6, 6.2 Hz, 2H), 4.42 (dd, J=8.8, 4.5 Hz, 1H), 4.47-4.61 (m, 8H), 5.19-5.22 (m, 4H), 5.29-5.35 (m, 4H), 5.83-5.94 (m, 4H), 7.21 (d, J=8.3 Hz, 2H), 7.44 (d, J=8.3 Hz, 2H), 8.57 (bs, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. custompurified by silica gel chromatography on a Biotage™ flash chromatography system

Sources & evidence

ORD record
ord-39d6be31969b4c71a6376ac012398208
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

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