2-Aminopyridine → N-[4-(2-pyridylamino-carbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine methyl ester

HRID 1493450Notes

Reaction equation

HRID 1493450 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:28][S:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:5][C:6](=[O:27])[C@H:7]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10](O)=[O:11].[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:28][S:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:5][C:6](=[O:27])[C@H:7]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:8][C@H:9]([C:10]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)=[O:11])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14997155N-[(S,S)-2,4-dibenzyl-4-carboxy-butyryl]-S-benzyl-(L)-cysteine methyl ester

Product 1

HCID 18645479N-[4-(2-pyridylamino-carbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.1 g of N-[(S,S)-2,4-dibenzyl-4-carboxybutyryl]-S-benzyl-(L)-cysteine methyl ester 0.60 g of 2-aminopyridine and 1.2 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 25 ml of methylene chloride is stirred at room temperature overnight. The mixture is concentrated, ethyl acetate is added and washed with water, sodium bicarbonate, dried (Na2SO4), filtered and concentrated. The residue is chromatographed on silica gel eluting with ethyl acetatemethylene chloride (1:9) to give N-[4-(2-pyridylaminocarbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine methyl ester (oil).

Workup

  1. concentrationThe mixture is concentrated
  2. additionethyl acetate is added
  3. washwashed with water, sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel eluting with ethyl acetatemethylene chloride (1:9)

Sources & evidence

ORD record
ord-5b016dc9251c4f8b8f66f367b1e8a11d
Source dataset
uspto-grants-1991_06
Patent number
US05021430

Reaction notes

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