N-[1(S)-(1H-imidazol-2-yl)-3-methylbutyl]-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester → n-[1(s)-(1h-Imidazol-2-yl)-3-methylbutyl]-3(r)-[3-[4-(pyridin-4-yl)phenyl]-1h-pyrrol-1-yl]succinamic acid formate salt

HRID 613894Notes

Reaction equation

HRID 613894 reaction equation
C([O:8][C:9](=[O:42])[CH2:10][C@@H:11]([N:25]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)=[CH:32][CH:31]=2)=[CH:26]1)[C:12]([NH:14][C@H:15]([C:20]1[NH:21][CH:22]=[CH:23][N:24]=1)[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])C1C=CC=CC=1>CCO.C1COCC1>[CH:9]([OH:42])=[O:8].[NH:24]1[CH:23]=[CH:22][N:21]=[C:20]1[C@@H:15]([NH:14][C:12](=[O:13])[C@H:11]([N:25]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[CH:32][C:33]([C:36]3[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=3)=[CH:34][CH:35]=2)=[CH:26]1)[CH2:10][C:9]([OH:42])=[O:8])[CH2:16][CH:17]([CH3:18])[CH3:19]

Participants

3

Reactant 1

HCID 53669781N-[1(S)-(1H-imidazol-2-yl)-3-methylbutyl]-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester

Product 1

HCID 70096923n-[1(s)-(1h-Imidazol-2-yl)-3-methylbutyl]-3(r)-[3-[4-(pyridin-4-yl)phenyl]-1h-pyrrol-1-yl]succinamic acid formate saltYield 81%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

According to the procedure described in Example 7(a), N-[1(S)-(1H-imidazol-2-yl)-3-methylbutyl]-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester was hydrogenolyzed in EtOH:THF (1:1) to yield in 81% yield N-[1(S)-(1H-imidazol-2-yl)-3-methylbutyl]-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid formate salt as a yellow amorphous solid. 1H NMR (DMSO-d6): δ 12.30 (bs, 1H), 8.65 (d, 1H, J=8.1 Hz), 8.59 (d, 2H, J=4.4 Hz), 8.13 (s, 1H), 7.75 (d, 2H, J=8.5 Hz), 7.71 (d, 2H, J=4.4 Hz), 7.60 (d, 2H, J=8.5 Hz), 7.34 (s, 1H), 6.91-6.83 (m, 3H), 6.44 (s, 1H), 5.08 (t, 1H, J=7.5 Hz), 4.97 (dd, 1H, J=8.1, 16.2 Hz), 3.10 (dd, 1H, J=8.1, 16.6 Hz), 2.90 (dd, 1H, J=7.2, 16.7 Hz), 1.68 (t, 2H, J=7.2 Hz), 1.52-1.45 (m, 1H), 0.86 (d, 3H, J=7.0 Hz), 0.83 (d, 3H, J=6.6 Hz). Anal. Calculated for C27H29N5O3.HCO2H.0.5 EtOAc: C, 64.15; H, 6.28; N, 12.47. Found: C, 64.21, H, 6.40; N, 12.60.

Sources & evidence

ORD record
ord-ee01b7c6b36a44eca4c89737a9692f7c
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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