Methyl 4-fluorosalicylate → Methyl 4-fluoro-2-(3-tert-butoxycarbonylaminopropoxy)benzoate

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23]O)=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[F:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:1][CH2:23][CH2:22][CH2:21][NH:20][C:18]([O:17][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:19])[CH:11]=1

Participants

Reactant 2

HCID 2775386Methyl 4-fluorosalicylate

HCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 57602453Methyl 4-fluoro-2-(3-tert-butoxycarbonylaminopropoxy)benzoateYield 84%

Procedure

Using a procedure analogous to Example 1-C, methyl 2-hydroxy-4-fluorobenzoate and 3-(tert-butoxycarbonylamino)propanol gave the desired product as a white solid (20.6 g, 84%). 1NMR IS-MS, m/e: 328 (m+1).

Sources & evidence

ORD record: ord-7703097fe671402eb56334e383416ee3
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700628B2

Reaction notes

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