2-acetoxy-1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanone → 2-Acetoxy-2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid ethyl ester

HRID 382205Notes

Reaction equation

HRID 382205 reaction equation
[C:1](OC(C1C=CN(C2C=CC(C3C=CC=CC=3)=CC=2)C=1)C(N1[C@@H](CC2C=CC=CC=2)COC1(C)C)=O)(=[O:3])[CH3:2].[CH2:39]([O:41][C:42](=[O:62])[CH:43]([C:45]1[O:49][C:48]([C:50]2[CH:55]=[CH:54][C:53]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:52][CH:51]=2)=[CH:47][CH:46]=1)[OH:44])[CH3:40]>>[CH2:39]([O:41][C:42](=[O:62])[CH:43]([O:44][C:1](=[O:3])[CH3:2])[C:45]1[O:49][C:48]([C:50]2[CH:55]=[CH:54][C:53]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)=[CH:52][CH:51]=2)=[CH:47][CH:46]=1)[CH3:40]

Participants

3

Reactant 2

HCID 183412742-acetoxy-1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanoneHCID 183415112-(2-Biphenyl-4-yl-furan-5-yl)-2-hydroxy-acetic acid ethyl ester

Product 1

HCID 183415082-Acetoxy-2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid ethyl esterYield 83%

Procedure

According to the procedure described in Example 13 for the preparation of 2-acetoxy-1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanone, 2-(2-biphenyl-4-yl-furan-5-yl)-2-hydroxy-acetic acid ethyl ester was acylated to furnish in 83% yield 2-acetoxy-2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid ethyl ester which was used without purification. Flash column chromatography with 0-20% EtOAc/hex as eluant gave an analytically pure pink solid, mp 136-140° C.

Sources & evidence

ORD record
ord-86a3340487f4405e88fb229a81721df4
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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