Dichloromethane methanol ammonium hydroxide → HCID 20672346, compound

HRID 1386724Notes

Reaction equation

HRID 1386724 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]2[C@@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:20][N:19]([C@H:28]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[C:29]([O:31]CC3C=CC(OC)=CC=3)=[O:30])[CH2:18]2)[CH2:12][CH2:11]1.C(Cl)Cl.CO.[NH4+].[OH-]>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][C@@H:17]2[C@@H:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][N:19]([C@H:28]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[C:29]([OH:31])=[O:30])[CH2:18]2)[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 57040067HCID 57040067, compound

Product 1

HCID 20672346HCID 20672346, compoundYield 94%

Procedure

The title compound was prepared from 58 mg (0.093 mmol) of 2-(R)-(3-(S)-((4-(3-(2-pyridyl)propyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, (4-methoxy)benzyl ester (from EXAMPLE 72, Step C) using a procedure analogous to that described in EXAMPLE 10, Step F. Flash chromatography using 90:10:1 v/v/v CH2Cl2/MeOH/NH4OH as the eluant afforded 44 mg (94%) of the title compound: 1H NMR (500 MHz) δ 0.82-3.90 (35H), 7.07-7.58 (8H), 8.49 (d, J=4.8 Hz, 11H); ESI-MS 504 (M+H).

Sources & evidence

ORD record
ord-f803acb7c3384d60ac1880e1608dc4a8
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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