(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)-acetic acid ethyl ester

HRID 382206Notes

Reaction equation

HRID 382206 reaction equation
C([C@H]1COC(C)(C)N1C(=O)CC1C=CN(C2C=CC(C3C=CC=CC=3)=CC=2)C=1)C1C=CC=CC=1.[CH2:35]([O:37][C:38](=[O:61])[CH:39](OC(=O)C)[C:40]1[O:44][C:43]([C:45]2[CH:50]=[CH:49][C:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:47][CH:46]=2)=[CH:42][CH:41]=1)[CH3:36]>>[CH2:35]([O:37][C:38](=[O:61])[CH2:39][C:40]1[O:44][C:43]([C:45]2[CH:50]=[CH:49][C:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:47][CH:46]=2)=[CH:42][CH:41]=1)[CH3:36]

Participants

3

Reactant 2

HCID 18341259(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-ethanoneHCID 183415082-Acetoxy-2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid ethyl ester

Product 1

HCID 183415102-(2-Biphenyl-4-yl-furan-5-yl)-acetic acid ethyl esterYield 61%

Procedure

According to the procedure described in Example 13 for the preparation of (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 was hydrogenolyzed to provide in 61% yield 2-(2-biphenyl-4-yl-furan-5-yl)-acetic acid ethyl ester as a white solid, mp 77-78° C.

Sources & evidence

ORD record
ord-1324f4cd5a3f46189cb54c3c62918105
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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