2-(2-Bromoethoxy)tetrahydro-2H-pyran → Methyl 3-(cyclopentyloxy)-4-methoxy-2-(N-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)acetamido)benzoate

HRID 1095772Notes

Reaction equation

HRID 1095772 reaction equation
[C:1]([NH:4][C:5]1[C:14]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:13]([O:21][CH3:22])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].Br[CH2:24][CH2:25][O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1>CN(C)C=O>[CH:16]1([O:15][C:14]2[C:5]([N:4]([CH2:24][CH2:25][O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[C:1](=[O:3])[CH3:2])=[C:6]([CH:11]=[CH:12][C:13]=2[O:21][CH3:22])[C:7]([O:9][CH3:10])=[O:8])[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 66781936Methyl 2-acetamido-3-(cyclopentyloxy)-4-methoxybenzoate

Product 1

HCID 66781726Methyl 3-(cyclopentyloxy)-4-methoxy-2-(N-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)acetamido)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-(cyclopentyloxy)-4-methoxy-2-(N-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)acetamido)benzoate was prepared from methyl 2-acetamido-3-(cyclopentyloxy)-4-methoxybenzoate (Example 1, Step 4) and 2-(2-bromoethoxy)-tetrahydro-2H-pyran following the procedure outlined in Example 4 (with the following exceptions: the solvent used was dimethylformamide, the reaction temperature was 33° C., and the reaction was conducted overnight). MS (ESI): 458.2 (M+Na).

Workup

  1. customwas 33° C.

Sources & evidence

ORD record
ord-0e2eef6b5f20474faebecc50dedc1edc
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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