Piperidine → tert-butyl[(1S)-4-[(tert-butoxycarbonyl)amino]-1-({[(2s)-2,5-diamino-5-oxopentanoyl]amino}methyl)butyl]carbamate

HRID 269651Notes

Reaction equation

HRID 269651 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]([C:24]([NH:26][CH2:27][C@@H:28]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:25])[CH2:19][CH2:20][C:21]([NH2:23])=[O:22])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C)C=O>[C:44]([O:43][C:41](=[O:42])[NH:40][C@H:28]([CH2:27][NH:26][C:24](=[O:25])[C@@H:18]([NH2:17])[CH2:19][CH2:20][C:21]([NH2:23])=[O:22])[CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])([CH3:45])([CH3:46])[CH3:47]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 708066899h-fluoren-9-ylmethyl{(1S)-4-amino-1-[({(2s)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-oxobutyl}carbamate

Product 1

HCID 88986898tert-butyl[(1S)-4-[(tert-butoxycarbonyl)amino]-1-({[(2s)-2,5-diamino-5-oxopentanoyl]amino}methyl)butyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 33 mg (0.05 mmol) of 9H-fluoren-9-ylmethyl{(1S)-4-amino-1-[({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-oxobutyl}carbamate (Example 129A) in 1 ml of dimethylformamide is stirred after the addition of 4 mg (0.05 mmol) of piperidine at room temperature for 45 min. The solvent is evaporated and the crude product is reacted without further purification.

Workup

  1. customThe solvent is evaporated
  2. customthe crude product is reacted without further purification

Sources & evidence

ORD record
ord-3c17c462b843499a943ae187e63c644a
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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