Trifluoroacetic acid → N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid

HRID 613925Notes

Reaction equation

HRID 613925 reaction equation
C([C@H](NC(=O)[C@H](C1OC(C2C=CC(C3C=CC=CC=3)=CC=2)=CC=1)CC(O)=O)CO)C1C=CC=CC=1.C([O:40][C:41](=[O:73])[CH2:42][CH:43]([C:56]1[O:60][C:59]([C:61]2[CH:66]=[CH:65][C:64]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)=[CH:63][CH:62]=2)=[CH:58][CH:57]=1)[C:44]([NH:46][C@H:47]([C:52](=[O:55])[NH:53][CH3:54])[C:48]([CH3:51])([CH3:50])[CH3:49])=[O:45])(C)(C)C.FC(F)(F)C(O)=O.CC(OC)(C)C>C(Cl)Cl>[CH3:49][C:48]([CH3:51])([CH3:50])[C@H:47]([NH:46][C:44](=[O:45])[CH:43]([C:56]1[O:60][C:59]([C:61]2[CH:62]=[CH:63][C:64]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)=[CH:65][CH:66]=2)=[CH:58][CH:57]=1)[CH2:42][C:41]([OH:73])=[O:40])[C:52](=[O:55])[NH:53][CH3:54]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 15413tert-Butyl methyl etherHCID 53815293N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propy]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid t-butyl esterHCID 54471073N-(1(S)-benzyl-2-hydroxyethyl)-3(S)-(2-biphenyl-4-yl-furan-5-yl)succinamic acid

Product 1

HCID 18341363N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acidYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the procedure described in Example 15(a) for the preparation of N-(1(S)-benzyl-2-hydroxyethyl)-3(S)-(2-biphenyl-4-yl-furan-5-yl)succinamic acid, N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid t-butyl ester was deprotected with trifluoroacetic acid in CH2Cl2 after 1 hour. Trituration of crude with MTBE/hex provided in 48% yield N-[2,2-dimethyl-1(S)-(methylcarbamoyl)propyl]-3-(2-(biphenyl-4-yl)-furan-5-yl)succinamic acid as a rust-colored amorphous solid. 1H NMR (CD3CN): δ 7.75 (d, 2H, J=8.5 Hz), 7.69-7.66 (m, 4H), 7.47 (t, 2H, J=7.2 Hz), 7.37 (t, 1H, J=7.2 Hz), 6.91 (d, 1H, J=7.7 Hz), 6.77 (d, 1H, J=3.3 Hz), 6.56 (bs, 1H), 6.39 (d, 1H, J=3.3 Hz), 4.24-4.19 (m, 1H), 4.12 (d, 1H, J=9.2 Hz), 3.17-3.08 (m, 1H), 2.82 (dd, 1H, J=5.0, 17.1 Hz), 2.67 (d, 3H, J=4.8 Hz), 0.86 (s, 9H). HRFABMS: Calculated for C27H31N2O5 (M+H+) 463.2233. Found: 463.2236.

Sources & evidence

ORD record
ord-41a65449ddf548cd9c6c9e13d6637161
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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