Chloroform → HCID 18391504, compound

HRID 1586110Notes

Reaction equation

HRID 1586110 reaction equation
C(OC(=O)[C@H]1C[C@H](OS(C2C=CC(C)=CC=2)(=O)=O)CN1C(OCC1C=CC=CC=1)=O)C.[C-]#N.[Na+].C(Cl)(Cl)Cl.[CH2:39]([O:41][C:42](=[O:60])[C@@H:43]1[CH2:47][C@H:46]([C:48]#[N:49])[CH2:45][N:44]1[C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH3:40]>CS(C)=O>[CH2:39]([O:41][C:42](=[O:60])[C@H:43]1[CH2:47][C@@H:46]([C:48]#[N:49])[CH2:45][N:44]1[C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH3:40]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8929Sodium CyanideHCID 14804603HCID 14804603, compoundHCID 18391505HCID 18391505, compound

Product 1

HCID 18391504HCID 18391504, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The tosylate 12 (2.02 g, 4.53 mmol) was treated with NaCN in DMSO at 80° C. to provide, after workup, the cis nitrile ester (0.88 g, 64%) as a colorless oil: [α]25D +32° (c 1.04, CHCl3); Spectra were identical in all respects to those of the enantiomer N-(benzyloxycarbonyl)-cis-4-cyano-L-proline ethyl ester; HRMS (EI, 22 eV) m/e 302.1255 (302.1266 calcd for C16H18NO4).

Workup

  1. customto provide

Sources & evidence

ORD record
ord-4586575ec075446a8da370b094771a66
Source dataset
uspto-grants-1999_08
Patent number
US05942537

Reaction notes

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