Triethylamine → HCID 53487859, compound

HRID 588819Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:26]([CH2:29]C)CC.ClC(OCC)=[O:33].[NH4+].[OH-]>C1COCC1.O>[C:29]([CH:9]1[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])(=[O:33])[NH2:26]

Participants

Conditions

Temperature: -2.5 °C

Procedure

To a solution of 1,4-di(tert-butoxycarbonyl)piperazine-2-carboxylic acid (8.21 g, 24.85 mmol) was dissolved in THF (50 mL) and Et3N (20 mL) at 0° C., ethyl chloroformate (2.8 g, 26.1 mmol) was added dropwise. After stirring at −5-0° C. for 1 h, NH4OH (20 mL) was added and the resulting solution was stirred at room temperature for 1 h. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 1N NaOH and brine, dried over Na2SO4 and concentrated in vacuo to give the product (7.5 g, 91.7% yield) as an off-white solid.

Workup

stirringthe resulting solution was stirred at room temperature for 1 h
extractionextracted with ethyl acetate
washThe organic layer was washed with 1N NaOH and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ff23a6bb6305417cb71deae5b967cb0e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227978B2

Reaction notes

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