Hydrochloric Acid → 1-Fmoc-4-Boc-Piperazine-2-acetic acid

HRID 30186

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][C:15]([O:17]C)=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH:20]1[C:32]2[CH:31]([CH2:33][O:34][C:35](Cl)=[O:36])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1>[OH-].[Na+]>[CH:20]1[C:32]2[CH:31]([CH2:33][O:34][C:35]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]3[CH2:14][C:15]([OH:17])=[O:16])=[O:36])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 5 °C

Procedure

3-Methoxycarbonylmethylpiperazine-1-carboxylic acid tert-butyl ester (6.0 g) was dissolved in TBF (60 ml) and 1N sodium hydroxide solution (60 ml) and stirred at room temperature for 6 hours. The solution was then cooled to 5° C. and adjusted to pH 9-10 by the addition of 10% hydrochloric acid. Nα(9-Fluorenylmethoxycarbonyl chloride (6.05 g) was then added portionwise, maintaining the pH at 9-10 by the addition of 1N NaOH solution. The reaction mixture was stirred at 5° C. for 16 hours. The solution was then adjusted to pH 1 by the addition of 10% hydrochloric acid. The solution was extracted with ethyl acetate (×2), dried (MgSO4) and evaporated. The title compound was obtained as a white foam (9.96 g), mass spectrum (API+) 411 [(M-C4H8)H+], C26H30N2O6 requires 466.

Workup

temperaturemaintaining the pH at 9-10
extractionThe solution was extracted with ethyl acetate (×2)
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-bd2c7ff1f3a949b6b56b20e3ea0f6d2b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423052B2

Linked notes

Loading…