2-Dimethylaminopyridine → Ethyl beta-[[2-[[(3-nitrophenyl)carbonyl]amino]acetyl]amino]pyridine-3-propanoate

HRID 378142

Reaction equation

HRID 378142 reaction equation
Cl.C([NH:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])C.[CH2:10]1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)[CH2:11]1.[N+:28]([C:31]1[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=1)[C:34]([NH:36][CH2:37][C:38]([OH:40])=O)=[O:35])([O-:30])=[O:29].CN([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1)C>CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>[N+:28]([C:31]1[CH:32]=[C:33]([C:34]([NH:36][CH2:37][C:38]([NH:4][CH:5]([C:52]2[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=2)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:40])=[O:35])[CH:41]=[CH:42][CH:43]=1)([O-:30])=[O:29]

Participants

7

Reactant 4

HCID 218852-DimethylaminopyridineHCID 94858Glycine, N-(3-nitrobenzoyl)-HCID 676246Di(succinimido) carbonateHCID 867595763-(Ethylamino)propanoic acid hydrochloride

Product 1

HCID 22608595Ethyl beta-[[2-[[(3-nitrophenyl)carbonyl]amino]acetyl]amino]pyridine-3-propanoateYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 11430Potassium CarbonateSolvent

Procedure

The same procedure used in the preparation of Example C was followed substituting an equivalent amount of DL-ethyl 3-amino-3-pyridyl propionate for ethyl beta-alanine hydrochloride. N,N'-Disuccinimidyl carbonate (14 g, 5.5 mmol) was added to 3-nitro-benzoyl glycine (10 g, 4.5 mmol) in dry dimethylformamide (30 mL) followed by dimethylaminopyridine (200 mg). After a period of 1 hour DL-ethyl 3-amino-3-(3-pyridyl) propionate dihydrochloride (13 g, 4.6 mmol) in 20% aqueous potassium carbonate (50 mL) was added in one portion. After complete reaction the product was collected by filtration (11.5 g, 80% yield). MS and 1H-NMR were consistent with the proposed structure.

Workup

  1. customThe same procedure used in the preparation of Example C
  2. customAfter complete reaction the product
  3. filtrationwas collected by filtration (11.5 g, 80% yield)

Sources & evidence

ORD record
ord-b5d2c8a532754646add25af6990ac224
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

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