N-(2,2-dimethyl-1(S)-(N-methylcarbamoyl)-propyl)-2-(2-biphenyl-4-yl-furan-5-yl)-acetamide → N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propy]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid t-butyl ester

HRID 382209Notes

Reaction equation

HRID 382209 reaction equation
[C:1]([O:5][C:6](=[O:43])[C@@H:7](C1C=CN(C2C=CC(C3C=CC=CC=3)=CC=2)C=1)CC(NN1[C@@H](CC2C=CC=CC=2)COC1(C)C)=O)([CH3:4])([CH3:3])[CH3:2].[CH3:44][C:45]([CH3:73])([CH3:72])[C@H:46]([NH:51][C:52](=[O:71])[CH2:53][C:54]1[O:58][C:57]([C:59]2[CH:64]=[CH:63][C:62]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:61][CH:60]=2)=[CH:56][CH:55]=1)[C:47](=[O:50])[NH:48][CH3:49].C([Li])CCC>>[C:1]([O:5][C:6](=[O:43])[CH2:7][CH:53]([C:54]1[O:58][C:57]([C:59]2[CH:60]=[CH:61][C:62]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:63][CH:64]=2)=[CH:56][CH:55]=1)[C:52]([NH:51][C@H:46]([C:47](=[O:50])[NH:48][CH3:49])[C:45]([CH3:73])([CH3:72])[CH3:44])=[O:71])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 18341365N-(2,2-dimethyl-1(S)-(N-methylcarbamoyl)-propyl)-2-(2-biphenyl-4-yl-furan-5-yl)-acetamideHCID 53794048N-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2(R)-(biphenyl-4-yl-1H-pyrrol-3-yl)succinamic acid t-butyl esterHCID 178418339Butyllithium

Product 1

HCID 53815293N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propy]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid t-butyl esterYield 7%

Procedure

According to the procedure described in Example 13 for the preparation of N-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2(R)-(biphenyl-4-yl-1H-pyrrol-3-yl)succinamic acid t-butyl ester, but N-(2,2-dimethyl-1(S)-(N-methylcarbamoyl)-propyl)-2-(2-biphenyl-4-yl-furan-5-yl)-acetamide was instead deprotonated with n-butyllithium (3.1 equiv) and alkylated to furnish 17 mg (7%) of N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid t-butyl ester as an amorphous solid.

Sources & evidence

ORD record
ord-9520bf251b784b2b99cae0d451cf67ab
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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