Ethylenediamine → 5-chloro-thiophene-2-carboxylic acid ((3S,4S)-1-{[2-fluoro-4-(2-oxo-oxazolidin-3-yl)-phenylcarbamoyl]-methyl}-4-methoxy-pyrrolidin-3-yl)-amide

HRID 1162714Notes

Reaction equation

HRID 1162714 reaction equation
C(O[C:4](=[O:22])[CH2:5][N:6]1[CH2:10][C@H:9]([O:11][CH3:12])[C@@H:8]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:7]1)C.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:34][CH2:33][O:32][C:31]2=[O:35])=[CH:26][C:25]=1[F:36].FC1C=C(I)C=CC=1N.O1CCNC1=O.C(N)CN.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[F:36][C:25]1[CH:26]=[C:27]([N:30]2[CH2:34][CH2:33][O:32][C:31]2=[O:35])[CH:28]=[CH:29][C:24]=1[NH:23][C:4]([CH2:5][N:6]1[CH2:10][C@H:9]([O:11][CH3:12])[C@@H:8]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:7]1)=[O:22]

Participants

8

Reactant 6

HCID 3301EthylenediamineHCID 62657Potassium Phosphate, TribasicHCID 739492-OxazolidinoneHCID 1856942-Fluoro-4-iodoanilineHCID 58748327{(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl esterHCID 686468883-(4-Amino-3-fluoro-phenyl)-oxazolidin-2-one

Product 1

HCID 587481625-chloro-thiophene-2-carboxylic acid ((3S,4S)-1-{[2-fluoro-4-(2-oxo-oxazolidin-3-yl)-phenylcarbamoyl]-methyl}-4-methoxy-pyrrolidin-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to example 25.3 {(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl ester (example 25.2) was reacted with 3-(4-amino-3-fluoro-phenyl)-oxazolidin-2-one (prepared from 2-fluoro-4-iodoaniline and 2-oxazolidinone in the presence of Cu(I)I, ethylenediamine and potassium phosphate in dioxane at 110° C.) to give 5-chloro-thiophene-2-carboxylic acid ((3S,4S)-1-{[2-fluoro-4-(2-oxo-oxazolidin-3-yl)-phenylcarbamoyl]-methyl}-4-methoxy-pyrrolidin-3-yl)-amide as yellow solid. MS 497.5 ([M+H]+)

Sources & evidence

ORD record
ord-0b25cd9a7b9442cab1c7aedfe9c5e61b
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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