1-Amino-3,3-diethoxypropane → 3-(3-(Phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)propyl 4-((1,3-dioxolan-2-yl)methyl)benzoate

HRID 332708Notes

Reaction equation

HRID 332708 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:30])[NH:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2]2.[O:31]1[CH2:35][CH2:34][O:33][CH:32]1[CH2:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1.NCCC(OCC)OCC>>[O:31]1[CH2:35][CH2:34][O:33][CH:32]1[CH2:36][C:37]1[CH:45]=[CH:44][C:40]([C:41]([O:29][CH2:28][CH2:27][CH2:26][O:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([CH:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:11][C:10]([O:9][C@@H:3]3[CH:4]4[CH2:5][CH2:6][N:1]([CH2:8][CH2:7]4)[CH2:2]3)=[O:30])[CH:20]=2)=[O:42])=[CH:39][CH:38]=1

Participants

4

Reactant 3

HCID 5210291-Amino-3,3-diethoxypropaneHCID 247269914-(1,3-Dioxolan-2-ylmethyl)benzoic acidHCID 117680437(R)-Quinuclidin-3-yl((3-(3-hydroxypropoxy)phenyl)(phenyl)methyl)carbamate

Product 1

HCID 710932903-(3-(Phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)propyl 4-((1,3-dioxolan-2-yl)methyl)benzoate

Procedure

The title compound was prepared as described in Chiral Example 11 Step 2 with (R)-quinuclidin-3-yl((3-(3-hydroxypropoxy)phenyl)(phenyl)methyl)carbamate and 4-(1,3-dioxolan-2-ylmethyl)-benzoic acid replacing 4-((3-(phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoic acid and 1-amino-3,3-diethoxypropane, respectively.

Sources & evidence

ORD record
ord-524c5b4df8eb41febab644e96cd03f8e
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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