(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 2300004Notes

Reaction equation

HRID 2300004 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 procdure 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. 1H NMR: δ 7.71 (d, 2H, J=8.5 Hz), 7.63-7.59 (m, 4H), 7.45 (t, 2H, J=7.4 Hz), 7.35 (t, 1H, J=7.4 Hz), 6.64 (d, 1H, J=2.9 Hz), 6.34 (d, 1H, J=3.3 Hz), 4.22 (q, 2H, J=7.2 Hz), 3.76 (s, 2H), 1.30 (t, 3H, J=7.2 Hz). Anal. Calculated for C20H18O3: C, 78.41; H, 5.92. Found: C, 78.16; H, 5.92.

Sources & evidence

ORD record
ord-52d540f24c4042129e0679820a4b9ff5
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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