Triethylamine → HCID 57190921, compound

HRID 1733654Notes

Reaction equation

HRID 1733654 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([OH:24])=O)[CH2:13][S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH2:31])[CH3:27].C(N(CC)CC)C.CS(ON=C(C#N)C(OCC)=O)(=O)=O>CN(C)C=O.C(OCC)(=O)C.O>[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH:31][C:22](=[O:24])[C@H:12]([CH2:13][S:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:27]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 98775N-[(Phenylmethoxy)carbonyl]-S-(phenylmethyl)-L-cysteineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 54531055Ethyl cyano{[(methanesulfonyl)oxy]imino}acetate

Product 1

HCID 57190921HCID 57190921, compoundYield 23.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl-S-benzyl-L-cysteine (1.73 g) and glycine ethyl ester hydrochloride (0.70 g) are dissolved in dimethylformamide (12 ml), and thereto are added triethylamine (1.40 ml) and further ethyl 2-methanesulfonyloxyimino-2-cyanoacetate (1.1 g). The mixture is allowed to stand at room temperature for 14 hours. To the reaction mixture are added water and ethyl acetate, and the ethyl acetate layer is separated, washed with water, 1 N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate and water in order and then dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off and the resulting residue is crystallized from ethanol-petroleum ether, separated by filtration and dried to give N-(N-benzyloxycarbonyl-S-benzyl-L-cysteinyl)glycine ethyl ester (0.5 g), melting point: 93°-95° C. The product is identified with an authentic sample by infrared spectrum.

Workup

  1. customthe ethyl acetate layer is separated
  2. washwashed with water, 1 N hydrochloric acid
  3. dry with materiala saturated aqueous sodium hydrogen carbonate and water in order and then dried over anhydrous magnesium sulfate
  4. customAfter drying
  5. distillationthe solvent is distilled off
  6. customthe resulting residue is crystallized from ethanol-petroleum ether
  7. customseparated by filtration
  8. customdried

Sources & evidence

ORD record
ord-064a2f6225b94b07b4b12e5539e36376
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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