2-Fluorobenzoic acid → HCID 45073031, compound

HRID 1810985Notes

Reaction equation

HRID 1810985 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19].C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1.Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:16]2[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=2[C:18]([OH:20])=[O:19])[CH2:10][C@@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 99352-Fluorobenzoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylate

Product 1

HCID 45073031HCID 45073031, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (S)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (4.10 g, 19.8 mmol) in pyridine (41 mL) is added 2-fluoro-benzoic acid (20.2 g. 140 mmol) followed by DBU (43 ml). The mixture is stirred at 150° C. for 48 h. The mixture is diluted with 600 mL of 2N HCl followed by extraction with EtOAc (3×300 mL). Organics are collected and purified by flash chromoatography to provide 3.50 g, 53% yield of (S)-4-(2-carboxy-phenyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. extractionfollowed by extraction with EtOAc (3×300 mL)
  2. customOrganics are collected
  3. custompurified by flash chromoatography

Sources & evidence

ORD record
ord-dda3f79f654b4e8dac3890355d6eceb6
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

Loading…