HCID 21180727, compound → HCID 131722791, compound

HRID 1386673Notes

Reaction equation

HRID 1386673 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([CH:25]([CH3:27])[CH3:26])[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:4]1)=O.[OH:28][C:29]1([CH2:35][CH2:36][CH2:37][C:38]2[CH:39]=[N:40][C:41]3[C:46]([CH:47]=2)=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[OH:28][C:29]1([CH2:35][CH2:36][CH2:37][C:38]2[CH:39]=[N:40][C:41]3[C:46]([CH:47]=2)=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:34][CH2:33][N:32]([CH2:1][C@@H:3]2[C@@H:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:6][N:5]([C@H:14]([CH:25]([CH3:27])[CH3:26])[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:4]2)[CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 21180727HCID 21180727, compound2×HCID 59924577HCID 59924577, compound

Product 1

HCID 131722791HCID 131722791, compoundYield 78.3%

Procedure

The title compound was prepared from 24 mg (0.067 mmol) of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-3-methylbutanoic acid, benzyl ester (from EXAMPLE 5, Step D) and 22.5 mg (0.073 mmol) of 4-hydroxy-4-(3-(quinolin-3-yl)propyl)piperidine.HCl from EXAMPLE 6, Step A using a procedure analogous to that described in EXAMPLE 1, Step J to provide 32.5 mg (75%) of the title compound: RF: 0.21 (19:1 v/v CH2Cl2/MeOH); 1H NMR (300 MHz) δ 0.88 (d, J=6.7,33H), 1.01 (d, J=6.7, 3H), 1.42-3.22 (m, 24H), 5.16 (ABq, 2H), 7.15-7.41 (m, 10H), 7.49-7.54 (m, 1H), 7.62-7.68 (m, 1H), 7.75 (d, J=8.0, 1H), 7.91 (s, 1H), 8.06 (d, J=8.2, 1H), 8.75 (d, J=2.1, 1H).

Sources & evidence

ORD record
ord-b91978f67a1a4b74b7b6a893f22d7892
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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