Methylhydrazine → HCID 56624470, compound

HRID 1462495Notes

Reaction equation

HRID 1462495 reaction equation
C1(=O)[N:5]([CH:6]2[CH2:11][S:10][C@H:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([CH2:18][C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[C:7]2=[O:28])C(=O)C2=CC=CC=C12.C(Cl)(Cl)Cl.CNN>CCOCC>[NH2:5][CH:6]1[CH2:11][S:10][C@H:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:8]([CH2:18][C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:25])[CH3:27])=[O:20])[C:7]1=[O:28]

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 6212ChloroformHCID 56636303HCID 56636303, compound

Product 1

HCID 56624470HCID 56624470, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of the trimethylsilyl ester product from part (b) (1.17 g., 2.36 mmole) in 4 ml. of dry chloroform is treated with N-methylhydrazine (217 mg., 4.72 mmole). The stoppered reaction is stirred at room temperature overnight, then diluted with ether and filtered to remove N-methyl-phthalhydrazide. Removal of organic solvents in vacuo yields (R)-dihydro-5-amino-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, 2-(trimethylsilyl)ethyl ester.

Workup

  1. customThe stoppered reaction
  2. filtrationfiltered
  3. customto remove N-methyl-phthalhydrazide
  4. customRemoval of organic solvents in vacuo

Sources & evidence

ORD record
ord-2eadd3688b3647dc8e4520194551da8d
Source dataset
uspto-grants-1984_07
Patent number
US04460579

Reaction notes

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