Hydrochloric Acid → HCID 20672426, compound

HRID 1386740Notes

Reaction equation

HRID 1386740 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]([CH2:27][CH:28]2[CH2:31][CH2:30][CH2:29]2)[C:15]([O:17]CC2C=CC(OC)=CC=2)=[O:16])[CH2:4]1)=O.[C:32]1([CH2:38][CH2:39][CH2:40][CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl.C(Cl)Cl.CO.[NH4+].[OH-]>>[C:32]1([CH2:38][CH2:39][CH2:40][CH:41]2[CH2:42][CH2:43][N:44]([CH2:1][C@@H:3]3[C@@H:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:6][N:5]([C@@H:14]([CH2:27][CH:28]4[CH2:29][CH2:30][CH2:31]4)[C:15]([OH:17])=[O:16])[CH2:4]3)[CH2:45][CH2:46]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 876784-(3-Phenylpropyl)piperidineHCID 21896990Dichloromethane methanol ammonium hydroxideHCID 53837226HCID 53837226, compound

Product 1

HCID 20672426HCID 20672426, compoundYield 64%

Procedure

The title compound was prepared from 25 mg (0.059 mmol) of 2-(S)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, (4-methoxy)benzyl ester (from EXAMPLE 92, Step C) and 14.3 mg (0.059 mmol) of 4-(3-phenylpropyl)piperidine.HCl using a procedures analogous to those described in EXAMPLE 1, Step J and EXAMPLE 10, Step F to 18.4 mg (64%) of the title compound: RF: 0.48 (90:10:1 v/v/v CH2Cl2/MeOH/NH4OH); 1H NMR (300 MHz, CD3OD) δ 0.99-3.67 (m, 33H), 6.96-7.23 (m, 10H); ESI-MS 489 (M+H); HPLC A: 2.69 min.

Workup

  1. custom2.69 min.

Sources & evidence

ORD record
ord-426f06c9b18c41669f9f20bb727f9748
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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