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

HRID 2381065Notes

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].CN([CH:26]=[O:27])C>>[CH:16]1([O:15][C:14]2[C:5]([N:4]([CH2:17][CH2:16][O:15][CH:14]3[CH2:13][CH2:12][CH2:11][CH2:26][O:27]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

Reactant 2

HCID 6228Dimethylformamide

HCID 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

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) following the procedure outlined in Example 4 (except: solvent was DMF; temp was 33° C.; time was overnight). MS (ESI): 458.2 (M+Na).

Sources & evidence

ORD record: ord-8d6af3c53f014d559c16d9f04b396f8b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258154B2

Reaction notes

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