Diethyl Ether → HCID 54765172, compound

HRID 469465Notes

Reaction equation

HRID 469465 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[S:10]1[CH:14]=[C:13]([C@@H:15]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]([O:18][C@@H:19]2[CH:24]3[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:12]2[CH:34]=[CH:35][CH:36]=[CH:37][C:11]1=2.C(OCC)C>CCOC(C)=O>[Cl-:1].[S:10]1[CH:14]=[C:13]([C@@H:15]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]([O:18][C@@H:19]2[CH:24]3[CH2:25][CH2:26][N+:21]([CH2:2][C:3](=[O:4])[C:5]4[S:6][CH:7]=[CH:8][CH:9]=4)([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:12]2[CH:34]=[CH:35][CH:36]=[CH:37][C:11]1=2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27579252-(Chloroacetyl)thiopheneHCID 58556993HCID 58556993, compound

Product 1

HCID 54765172HCID 54765172, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-(thiophen-2-yl)ethanone (32.7 mg, 0.20 mmol) was added to a solution of (R)—((R)-quinuclidin-3-yl) 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (diastereomer 1 of C19) (80 mg, 0.20 mmol) in EtOAc (3 ml). The reaction was stirred at r.t. overnight. Diethylether (10 ml) was added, and the precipitate was collected and dried under vacuum to obtain (R)-3-((R)-2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (101 mg, 90% yield).

Workup

  1. customthe precipitate was collected
  2. customdried under vacuum

Sources & evidence

ORD record
ord-454e5ca497004b6f854d58735f70f1e6
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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