Dimethylformamide → HCID 10602177, compound

HRID 1653683

Reaction equation

HRID 1653683 reaction equation
[CH3:1]N(C=O)C.[NH2:6][C:7]1[N:8]=[C:9]([NH2:27])[C:10]2[C:15]([CH2:16][CH2:17][C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)=[CH:14][NH:13][C:11]=2[N:12]=1.[C:28]([O:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][C@@H:39]([C:41]([OH:43])=[O:42])[NH2:40])=[O:34])([CH3:31])([CH3:30])[CH3:29].P(C#N)(OCC)(OCC)=O>C(N(CC)CC)C>[NH2:6][C:7]1[N:8]=[C:9]([NH2:27])[C:10]2[C:15]([CH2:16][CH2:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH:40][C@H:39]([C:41]([O:43][CH3:1])=[O:42])[CH2:38][CH2:37][CH2:36][NH:35][C:33]([O:32][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:34])=[O:23])=[CH:20][CH:19]=3)=[CH:14][NH:13][C:11]=2[N:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 6993436(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acidHCID 104473314-[2-(2,4-diamino-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoic acid

Product 1

HCID 10602177HCID 10602177, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a DMF solution of 4-[2-(2,4-diamino-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoic acid (1.52 g) and methyl ester of N(δ)-t-butyloxycarbonyl-L-ornithine (1.3 g) was added diethyl cyanophosphate (1.4 g). The mixture was stirred for one hour at room temperature in the presence of triethylamine (3.0 g). The reaction mixture was concentrated under reduced pressure. The concentrate was purified by column chromatography on silica gel (carrier: 30 g; chloroform:ethanol containing 1% ammonium=20:1-15:1) to afford methyl N(α)-[4-[2-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-N-(δ)-(t-butyloxycarbonyl)-L-ornithinate (2.30 g; yield 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe concentrate was purified by column chromatography on silica gel (carrier: 30 g; chloroform:ethanol containing 1% ammonium=20:1-15:1)

Sources & evidence

ORD record
ord-6c87443a3ce54b5fa4461fbfe227b526
Source dataset
uspto-grants-1995_04
Patent number
US05403843

Linked notes

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