Acetyl chloride → HCID 22844246, compound

HRID 1197004Notes

Reaction equation

HRID 1197004 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][NH:6][C:7](=[O:33])[C@H:8]([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])[NH2:9])[CH3:2].[C:35](Cl)(=[O:37])[CH3:36].C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][NH:6][C:7](=[O:33])[C@H:8]([C:10]([S:13][C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH3:12])[CH3:11])[NH:9][C:35](=[O:37])[CH3:36])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22844258HCID 22844258, compound

Product 1

HCID 22844246HCID 22844246, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of S-trityl-L-penicillamylglycine ethyl ester (C-2) (3.7 g) in dichloromethane (50 ml) were added acetyl chloride (0.66 ml) and triethylamine (0.88 ml) at 0° C. The mixture was stirred at the same temperature for 15 minutes and then ice water was added. The organic layer was washed with an aqueous potassium hydrogensulfate solution, water, an aqueous sodium hydrogencarbonate solution, water and saturated saline, in this order, and dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was subjected to silica gel column chromatography, to give N-acetyl-S-trityl-L-penicillamylglycine ethyl ester (3.5 g).

Workup

  1. washThe organic layer was washed with an aqueous potassium hydrogensulfate solution, water
  2. dry with materialan aqueous sodium hydrogencarbonate solution, water and saturated saline, in this order, and dried over magnesium sulfate
  3. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b587c44a231e4794a17abbe3d270a03f
Source dataset
uspto-grants-1992_05
Patent number
US05116861

Reaction notes

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