Methanol → HCID 54419438, compound

HRID 2299951Notes

Reaction equation

HRID 2299951 reaction equation
C([O:8][C:9](=[O:42])[CH2:10][C@@H:11]([N:22]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39](=[O:41])[NH2:40])=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)=[CH:23]1)[C:12]([NH:14][C@@:15]([CH3:21])(O)[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:13])C1C=CC=CC=1.C[OH:44]>CCOC(C)=O>[C:39]([C:36]1[CH:35]=[CH:34][C:33]([C:30]2[CH:31]=[CH:32][C:27]([C:24]3[CH:25]=[CH:26][N:22]([C@@H:11]([C:12]([NH:14][C@H:15]([CH2:21][OH:44])[C:16]([CH3:18])([CH3:17])[CH3:19])=[O:13])[CH2:10][C:9]([OH:8])=[O:42])[CH:23]=3)=[CH:28][CH:29]=2)=[CH:38][CH:37]=1)(=[O:41])[NH2:40]

Participants

4

Reactant 2

HCID 887MethanolHCID 70099412HCID 70099412, compound

Product 1

HCID 54419438HCID 54419438, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

According to the procedures described in Example 1(a), 3(R)-[3-(4′-carbamoylbiphenyl-4-yl)-1H-pyrrol-1-yl]-N-(1(S)-hydroxy-methyl-2,2-dimethyl-propyl)succinamic acid benzyl ester in MeOH and EtOAc was hydrogenolyzed to afford in 88% yield 3(R)-[3-(4′-carbamoylbiphenyl-4-yl)-1H-pyrrol-1-yl]-N-(1(S)-hydroxymethyl-2,2-dimethyl-propyl)succinamic acid as a white powder, mp 192-4° C. 1H NMR (CD3OD): δ 7.95 (d, 2H, J=8.4 Hz), 7.72 (d, 2H, J=8.1 Hz), 7.60 (s, 4H), 7.32 (d, 1H, J=1.6 Hz), 6.92 (t, 1H, J=2.5 Hz), 6.51 (s, 1H), 5.20 (t, 1H, J=7.5 Hz), 3.85-3.75 (m, 2H), 3.02 (dd, 1H, J=7.2, 17.0 Hz), 0.92 (s, 9H). IR (KBr): 3360, 2961, 1710, 1658, 1404, 1201, 770 cm1; HRFABMS: Calculated for C27H32N3O5 (M+H)+: 478.2342. Found: 478.2360. Anal. Calculated for C27H32N3O5 (M+H)+. 478.2342. Found: 478.2360. Anal Calculated for C27H31N3O5.0.25CH2Cl2: C, 65.62; H, 6.37; N, 8.42. Found: C, 65.86, H, 6.69; N, 8.30.

Sources & evidence

ORD record
ord-0d5b90f468f943ffae71fdfc56d5f04c
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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