2,6-Lutidine → HCID 22844258, compound

HRID 1197003Notes

Reaction equation

HRID 1197003 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[CH2:5][NH:6][C:7](=[O:40])[C@H:8]([C:17]([S:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:19])[CH3:18])[NH:9]C(OC(C)(C)C)=O)[CH3:2].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:41])[CH2:5][NH:6][C:7](=[O:40])[C@H:8]([C:17]([S:20][C:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:19])[CH3:18])[NH2:9])[CH3:2]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 22844257HCID 22844257, compound

Product 1

HCID 22844258HCID 22844258, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of N-t-butoxycarbonyl-S-trityl-L-penicillamylglycine ethyl ester (B-2) (4.5 g) and 2,6lutidine (2.8 ml) in dichloromethane (100 ml), was added dropwise at 0° C. the solution of trimethylsilyl trifluoromethanesulfonate (3.9 ml), and the mixture was stirred for 1 hour while the temperature was gradually returned to the room temperature. To the reaction mixture was added ice-water, and the organic layer was washed with 1N-hydrochloric acid, water, an aqueous solution of sodium hydrogencarbonate, water, and saturated saline, in this order, and dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, to give S-trityl-L-penicillamylglycine ethyl ester (3.8 g)

Workup

  1. customwas gradually returned to the room temperature
  2. washthe organic layer was washed with 1N-hydrochloric acid, water
  3. dry with materialan aqueous solution of sodium hydrogencarbonate, water, and saturated saline, in this order, and dried over magnesium sulfate
  4. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-d1a6480ba59a42bfa575cd52511f2274
Source dataset
uspto-grants-1992_05
Patent number
US05116861

Reaction notes

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