2,6-Lutidine → HCID 22844259, compound

HRID 1197005Notes

Reaction equation

HRID 1197005 reaction equation
C(OC([NH:8][C@H:9]([C:33]([NH:35][C@H:36]([C:48]([OH:50])=[O:49])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1)=[O:34])[C:10]([S:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:12])[CH3:11])=O)(C)(C)C.C([N+](CCCC)(CCCC)CCCC)CCC.N1C(C)=CC=CC=1C.FC(F)(F)S([O-])(=O)=O>ClCCl>[C:14]([S:13][C:10]([CH3:12])([CH3:11])[C@@H:9]([C:33]([NH:35][C@H:36]([C:48]([OH:50])=[O:49])[CH2:37][C:38]1[CH:39]=[CH:40][C:41]([S:44]([OH:47])(=[O:45])=[O:46])=[CH:42][CH:43]=1)=[O:34])[NH2:8])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2758875TrifluoromethanesulfonateHCID 86745855HCID 86745855, compound

Product 1

HCID 22844259HCID 22844259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of tetrabutylammonium N-t-butoxycarbonyl-S-trityl-L-penicillamyl-p-sulfophenylalanine (B-23)(7.5 g) and 2,6-lutidine (3.8 ml) in dichloromethane (100 ml), was added dropwise at 0° C. the solution of trimethylsylyl trifluoromethanesulfonate (5.5 ml), and the mixture was stirred for 1 hour while the temperature was gradually returned to the room temperature. The solvent was evaporated off under reduced pressure and the residue was washed with diethyl ether and acetone, in this order, to give S-trityl-L-penicillamyl-p-sulfophenylalanine (3.lg).

Workup

  1. customwas gradually returned to the room temperature
  2. customThe solvent was evaporated off under reduced pressure
  3. washthe residue was washed with diethyl ether and acetone, in this order

Sources & evidence

ORD record
ord-cef743b7443849d0ad4c33d8f8523b33
Source dataset
uspto-grants-1992_05
Patent number
US05116861

Reaction notes

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