Methyl 4-aminobenzoate → Methyl 4-(2-cyclopentylacetamido)-2-fluorobenzoate

Reaction equation

[CH:1]1([CH2:6][C:7](Cl)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([F:21])[CH:12]=1.NC1C=CC(C(OC)=O)=CC=1>>[CH:1]1([CH2:6][C:7]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([F:21])[CH:12]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 12082Methyl 4-aminobenzoate

HCID 3485182Cyclopentylacetyl chloride

HCID 21957875Methyl 4-amino-2-fluorobenzoate

Product 1

HCID 86701957Methyl 4-(2-cyclopentylacetamido)-2-fluorobenzoate

Procedure

The title compound was prepared as described in Example 52A, substituting 2-cyclopentylacetyl chloride for 2-cyclopentylacetyl chloride and methyl 4-amino-2-fluorobenzoate for methyl 4-aminobenzoate.

Sources & evidence

ORD record: ord-286c9df4e2c2491fab9e1b2fe525b7e2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187472B2

Reaction notes

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