Diisopropylethylamine → Boc-D-phenylalanylproline (6-cyano-3-picolyl)amide

HRID 1282281Notes

Reaction equation

HRID 1282281 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][N:13]=1)#[N:11].[NH:20]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@@H:21]([C:29]([N:31]1[CH2:38][CH2:37][CH2:36][C@H:32]1[C:33](O)=[O:34])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:10]([C:12]1[N:13]=[CH:14][C:15]([CH2:18][NH:19][C:33](=[O:34])[C@@H:32]2[CH2:36][CH2:37][CH2:38][N:31]2[C:29](=[O:30])[C@@H:21]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:20][C:39]([O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[O:40])=[CH:16][CH:17]=1)#[N:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1797945Boc-D-phe-pro-OHHCID 113557155-(Aminomethyl)picolinonitrile

Product 1

HCID 54405429Boc-D-phenylalanylproline (6-cyano-3-picolyl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8.12 g of diisopropylethylamine and subsequently 11 ml (15 mmol) of propanephosphonic anhydride (50% strength solution in ethyl acetate) were added dropwise to a solution of 2.11 g (12.5 mmol) of 2-cyano-5-(aminomethyl)pyridine and 4.5 g (12.5 mmol) of Boc-D-Phe-Pro-OH in 70 ml of CH2Cl2 at −5° C. The mixture was then stirred for 2 h, during which the temperature was allowed to rise from −5° to 20° C. The organic phase was washed with water, 5% strength sodium bicarbonate and 5% strength citric acid solutions, dried over Na2SO4 and evaporated to dryness. A pale yellowish crystalline residue was obtained, melting point 167-170° C., and was used without further purification in the next reaction.

Workup

  1. customto rise from −5° to 20° C
  2. washThe organic phase was washed with water, 5% strength sodium bicarbonate and 5% strength citric acid solutions
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customA pale yellowish crystalline residue was obtained
  6. custommelting point 167-170° C., and was used without further purification in the next reaction

Sources & evidence

ORD record
ord-fc1243ff1bfd4ea7a9a367fd000386af
Source dataset
uspto-grants-2002_09
Patent number
US06455671B1

Reaction notes

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