Cesium carbonate → 3-(1,1-Dimethylethyl) 1,2-bis(phenylmethyl) 1,2,3-pyrazolidinetricarboxylate

HRID 1396840Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:30]([CH2:38][CH2:39]Br)[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>C(#N)C>[N:11]1([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:39][CH2:38][CH:30]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:12]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of bis(benzyloxycarbonyl)hydrazine (2.65 g, 8.83 mol) in acetonitrile (30 L) was charged into 100 L-reactor. Cesium carbonate (6.00 kg, 18.4 mol) and tert-butyl 2,4-dibromobutyrate (2.65 kg, 8.83 mol) were added into the above solution. The mixture solution was heated at 50° C. for 2.5 h until the two starting materials were completely consumed. The mixture solution was cooled to room temperature. A filtration was performed to remove some undissolved materials. The filtrate was concentrated under vacuum to afford product (4000 g crude product) as a brown oil.

Workup

customwere completely consumed
temperatureThe mixture solution was cooled to room temperature
filtrationA filtration
customto remove some undissolved materials
concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record: ord-df41402dcf2c49969e18cb4fb1077656
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901119B2

Reaction notes

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