4-Methylmorpholine → (R)-1-[[2-[2-[(R)-2-ethylcarbonyl-2,5-dihydropyrrole-1-yl]-2-oxo-ethoxyl]-phenoxy]acetyl]-2,5-dihydropyrrole-2-carboxylic acid ethyl ester

HRID 1583216Notes

Reaction equation

HRID 1583216 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[CH2:8]([O:10][C:11]([C@H:13]1[CH:17]=[CH:16][CH2:15][NH:14]1)=[O:12])[CH3:9].[C:18]1([O:29][CH2:30][C:31]([OH:33])=O)[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH2:25][C:26]([OH:28])=O.C[N:35]1[CH2:40][CH2:39]O[CH2:37][CH2:36]1.O.ON1C2C=CC=C[C:46]=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH2:8]([O:10][C:11]([C@H:13]1[CH:17]=[CH:16][CH2:15][N:14]1[C:26](=[O:28])[CH2:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:29][CH2:30][C:31]([N:35]1[CH2:40][CH:39]=[CH:37][C@@H:36]1[C:3]([CH2:2][CH3:46])=[O:5])=[O:33])=[O:12])[CH3:9]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 794272,2'-(1,2-Phenylenebis(oxy))bisacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69895296(R)-2,5-dihydro-1H-pyrrole-2-carboxylic acid ethyl ester trifluoroacetate

Product 1

HCID 57160914(R)-1-[[2-[2-[(R)-2-ethylcarbonyl-2,5-dihydropyrrole-1-yl]-2-oxo-ethoxyl]-phenoxy]acetyl]-2,5-dihydropyrrole-2-carboxylic acid ethyl esterYield 65.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.99 g (0.003 mol) (R)-2,5-dihydro-1H-pyrrole-2-carboxylic acid ethyl ester trifluoroacetate (1:1), 0.34 g (0.0015 mol) 1,2-phenylenedioxydiacetic acid, 1.3 ml (0.012 mol) N-methylmorpholine, and 0.46 g (0.003 mol) 1-hydroxybenzotriazole hydrate in 80 ml dichloromethane were added 0.57 g (0.003 mol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimid hydrochloride. After stirring at room temperature for 18 hours the mixture was extracted with 1N HCl, water, 10% aqueous sodium bicarbonate and again water. Chromatography over silicagel with ethylacetate yielded 0.45 g (32%) (R)-1-[[2-[2-[(R)-2-ethylcarbonyl-2,5-dihydropyrrole-1-yl]-2-oxo-ethoxyl]-phenoxy]acetyl]-2,5-dihydropyrrole-2-carboxylic acid ethyl ester as colorless oil. ISP-MS: 473 (MH)+.

Workup

  1. extractionwas extracted with 1N HCl, water, 10% aqueous sodium bicarbonate and again water

Sources & evidence

ORD record
ord-0a696e3095a1431fa05dd784b89d9555
Source dataset
uspto-grants-2004_05
Patent number
US06740760B2

Reaction notes

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