Dichloromethane methanol ammonium hydroxide → HCID 20672396, compound

HRID 1386726Notes

Reaction equation

HRID 1386726 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C@@H:21]2[C@@H:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:24][N:23]([C@H:32]([CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)[C:33]([O:35]CC3C=CC(OC)=CC=3)=[O:34])[CH2:22]2)[CH2:16][CH2:15]1.C(Cl)Cl.CO.[NH4+].[OH-]>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C@@H:21]2[C@@H:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:24][N:23]([C@H:32]([CH:45]3[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]3)[C:33]([OH:35])=[O:34])[CH2:22]2)[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 57177561HCID 57177561, compound

Product 1

HCID 20672396HCID 20672396, compoundYield 90.1%

Procedure

The title compound was prepared from 77 mg (0.11 mmol) of 2-(R)-(3-(S)-((4-(3-(quinoxalin-2-yl)propyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, (4-methoxy)benzyl ester (from EXAMPLE 73, Step B) using a procedure analogous to that described in EXAMPLE 10, Step F. Flash chromatography using 95:5:0.5 v/v/v CH2Cl2/MeOH/NH4OH as the eluant afforded 55 mg (87%) of the title compound: 1H NMR (500 MHz) δ 0.874.00 (35H), 7.22-7.30 (5H), 7.69-7.76 (2H), 8.00-8.08 (2H), 8.70 (s, 1H); ESI-MS 555 (M+H); HPLC A: 2.27 min.

Sources & evidence

ORD record
ord-b6ca1906f47847e083337d4b762d1af8
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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