tert-Butyl piperazine-1-carboxylate → HCID 69228209, compound

HRID 2220835Notes

Reaction equation

HRID 2220835 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[F:8].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.O.[C:26]([OH:30])(=[O:29])[CH:27]=O>C(Cl)Cl>[C:21]([O:20][C:18]([N:12]1[CH2:17][CH2:16][N:15]([CH:27]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)[C:26]([OH:30])=[O:29])[CH2:14][CH2:13]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 69228209HCID 69228209, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The requisite [4-(tert-butoxycarbonyl)piperazin-1-yl](3-chloro-4-fluorophenyl)acetic acid was synthesized using the following method. (3-Chloro-4-fluorophenyl)boronic acid (440 mg, 2.52 mmol), tert-butyl piperazine-1-carboxylate (469 mg, 2.52 mmol) and glyoxylic acid monohydrate (232 mg, 2.52 mmol) were reacted together in DCM (10 mL) at reflux overnight. The volatiles were removed under reduced pressure. Chromatography of the residue on SiO2 (0-10% MeOH:DCM) afforded the title compound (767 mg, 82%). MS m/z 373.1 (M+H)+, 317.1 (M+H-t-butyl). 1H NMR (300.1 MHz, DMSO) δ12.80 (s, 0.6H), 7.59(d, J=7.2 Hz, 1H), 7.42 (d, J=7.2 Hz, 2H), 4.09(s, 1H), 3.30 (s, 2H), 3.16 (s, 2H), 2.35 (m, 4H), 1.38 (s, 9H).

Workup

  1. temperatureat reflux overnight
  2. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-5383605ce46440ab90abac7fa2231dd4
Source dataset
uspto-grants-2008_05
Patent number
US07368448B2

Reaction notes

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