Piperidine → HCID 86762029, compound

HRID 39272Notes

Reaction equation

HRID 39272 reaction equation
C1C2C(COC([NH:18][C@H:19]([C:42]([OH:44])=[O:43])[CH2:20][CH2:21][C:22](=[O:41])[NH:23][CH:24]([P:33]([CH2:38][CH:39]=[CH2:40])([CH2:35][CH:36]=[CH2:37])=[O:34])[P:25]([CH2:30][CH:31]=[CH2:32])([CH2:27][CH:28]=[CH2:29])=[O:26])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[CH2:30]([P:25]([CH:24]([P:33]([CH2:35][CH:36]=[CH2:37])([CH2:38][CH:39]=[CH2:40])=[O:34])[NH:23][C:22](=[O:41])[CH2:21][CH2:20][C@@H:19]([C:42]([OH:44])=[O:43])[NH2:18])([CH2:27][CH:28]=[CH2:29])=[O:26])[CH:31]=[CH2:32]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86762030N2-(9-fluorenylmethoxycarbonyl)-N5-(bis(diallylphosphoryl)methyl)-L-glutamine

Product 1

HCID 86762029HCID 86762029, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Fmoc-protected compound 97 (898 mg, 1.18 mmol) was treated with a 5% v/v solution of piperidine in DMF (5.9 mL). After stirring for 4 h, the reaction mixture was concentrated to dryness and purified by silica gel chromatography on a Biotage™ flash chromatography system using a gradient of 0-5% methanol in CH2Cl2. Compound 98 was obtained as a colorless oil (274 mg, 43%). 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.72-1.81 (m, 1H), 2.04-2.31 (m, 3H), 2.36-2.43 (m, 1H), 2.46-2.54 (m, 1H), 3.41 (dd, J=9.5, 4.3 Hz, 1H), 4.59-4.67 (m, 8H), 5.15 (dt, J=22.1, 9.1 Hz, 1H), 5.23-5.26 (m, 4H), 5.35-5.39 (m, 4H), 5.88-5.98 (m, 4H), 7.50 (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-3a8b5594187a4723864b575a9b1ff31f
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

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