Dichloromethane → 1-(4(S)-benzyl-oxazolidin-2-on-3-yl)-2-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-ethanone

HRID 382193Notes

Reaction equation

HRID 382193 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[CH:18][C:17]([CH2:20]C(O)=O)=[CH:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[CH2:24]([C@H:31]1[CH2:35][O:34][C:33](=[O:36])[N:32]1[C:37](=[O:51])CC1C=CN(C2C=CC(F)=CC=2)C=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([C@H]1COC(=O)N1)C1C=CC=CC=1.CCOC(C)=O.C(Cl)Cl>CCOC(C)=O.CC(OC)(C)C>[CH2:24]([C@H:31]1[CH2:35][O:34][C:33](=[O:36])[N:32]1[C:37](=[O:51])[CH2:20][C:17]1[CH:18]=[CH:19][N:15]([C:12]2[CH:11]=[CH:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[CH:14][CH:13]=2)[CH:16]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 206968641-(4(S)-benzyl-oxazolidin-2-on-3-yl)-2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-ethanone 2-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-acetic acid

Product 1

HCID 183412661-(4(S)-benzyl-oxazolidin-2-on-3-yl)-2-[1-(4'-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-ethanoneYield 59%

Reagents, catalysts & solvents 1

HCID 18176222EtOAc MTBESolvent

Procedure

As in Example 14(a) for 1-(4(S)-benzyl-oxazolidin-2-on-3-yl)-2-[1-(4-fluorophenyl)-1H-pyrrol-3-yl]-ethanone 2-[1-(4′-cyanobiphenyl-4-yl)-1H-pyrrol-3-yl]-acetic acid and 4(S)-benzyl-2-oxazolidinone were coupled. Flash column chromatography with 10-25% EtOAc/hex to CH2Cl2 stepwise gradient eluant and subsequent trituration with EtOAc/MTBE/hex provided in 59% yield 1-(4(S)-benzyl-oxazolidin-2-on-3-yl)-2-[1-(4′-cyanobiphenyl4-yl)-1H-pyrrol-3-yl]-ethanone as a pale yellow amorphous solid.

Sources & evidence

ORD record
ord-7662ea7ff1b3411d9093356310729d08
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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