3-Aminobenzyl alcohol → (R)-Quinuclidin-3-yl ((S)-(3-(2-((3-(hydroxymethyl)phenyl)amino)-2-oxoethoxy)phenyl)(phenyl)methyl)carbamate

HRID 874838Notes

Reaction equation

HRID 874838 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[C:10]1([C@H:16]([NH:28][C:29]([O:31][C@@H:32]2[CH:37]3[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]3)[CH2:33]2)=[O:30])[C:17]2[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=2)[O:20][CH2:21][C:22](O)=[O:23])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1([C@H](NC(O[C@@H]2C3CCN(CC3)C2)=O)C2C=C(C=CC=2)OCC2C=CC(C(O)=O)=CC=2)C=CC=CC=1>>[N:34]12[CH2:35][CH2:36][CH:37]([CH2:38][CH2:39]1)[C@@H:32]([O:31][C:29](=[O:30])[NH:28][C@H:16]([C:17]1[CH:27]=[CH:26][CH:25]=[C:19]([O:20][CH2:21][C:22]([NH:1][C:2]3[CH:9]=[CH:8][CH:7]=[C:4]([CH2:5][OH:6])[CH:3]=3)=[O:23])[CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:33]2

Participants

4

Reactant 3

HCID 802933-Aminobenzyl alcoholHCID 867208154-((3-((S)-Phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)-phenoxy)methyl)benzoic acidHCID 901981392-(3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)-methyl)phenoxy)acetic acid

Product 1

HCID 90203069(R)-Quinuclidin-3-yl ((S)-(3-(2-((3-(hydroxymethyl)phenyl)amino)-2-oxoethoxy)phenyl)(phenyl)methyl)carbamate

Procedure

The title compound was prepared as described in Example 1 Step 11 with 3-aminobenzyl alcohol and 2-(3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)-methyl)phenoxy)acetic acid replacing 3-(1,3-dioxolan-2-yl)propyl piperidine-4-carboxylate hydrochloride and 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)-amino)methyl)phenoxy)methyl)benzoic acid respectively. Crude material used directly in the next step without further purification.

Workup

  1. customCrude material used directly in the next step without further purification

Sources & evidence

ORD record
ord-e7be00599826402191bd6b30c57676b1
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

Loading…