Cesium carbonate → HCID 59279885, compound

HRID 2045707Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].BrC1C=CC(S([O:17][C@@H:18]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)(=O)=O)=CC=1.[Br:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][C:44]=1[O:45][CH3:46])[NH:41][C:40](=[O:47])[CH:39]=[C:38]2O>CN1C(=O)CCC1>[Br:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][C:44]=1[O:45][CH3:46])[NH:41][C:40](=[O:47])[CH:39]=[C:38]2[O:17][C@H:18]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]1

Participants

Conditions

Temperature: 60 °C

Procedure

Cs2CO3 (8.42 g, 25.8 mmol) was added to a solution of 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (4 g, 8.61 mmol) and the product from step 1 (3.49 g, 12.92 mmol) in NMP (86 ml) under nitrogen. The mixture was then heated to 60° C. After 6.5 h, the reaction was extracted with water and EtOAc. The organic layer was extracted with water and brine and dried over MgSO4. The solvent was then removed in vacuo. The crude product (6.5 g) was purified on silica (gradient elution, 0-100% EtOAc/hexanes, and then 0-5% MeOH/DCM) to yield 2.26 g (53%) of the title compound. LRMS ESI+ ((M-Boc)+H)+ 397.3/399.3.

Workup

extractionthe reaction was extracted with water and EtOAc
extractionThe organic layer was extracted with water and brine
dry with materialdried over MgSO4
customThe solvent was then removed in vacuo
customThe crude product (6.5 g) was purified on silica (
washgradient elution, 0-100% EtOAc/hexanes

Sources & evidence

ORD record: ord-bef46001d7c84355aa519de1f1fe297d
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591878B2

Reaction notes

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