3-(Methylthio)propylamine → HCID 20285453, compound

HRID 127618Notes

Reaction equation

HRID 127618 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH2:6].C(=O)(O)[O-].[Na+].[C:12]([O:15][C:16]([CH3:20])([CH3:19])[CH2:17]Br)(=[O:14])[CH3:13]>C(O)C>[C:16]([O:15][C:12](=[O:14])[CH2:13][NH:6][CH2:5][CH2:4][CH2:3][S:2][CH3:1])([CH3:20])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 777433-(Methylthio)propylamineHCID 516892Sodium BicarbonateHCID 197628551-Bromo-2-methylpropan-2-yl acetate

Product 1

HCID 20285453HCID 20285453, compoundYield 116.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-methylthiopropylamine (30.0 g, 0.285 mol) and sodium bicarbonate (12.0 g, 0.142 mol) in 250 ml of ethanol was added dropwise bromo-t-butyl acetate (27.8 g, 0.142 mol). After 5 hours the ethanol was removed on a rotary evaporator and the residue partitioned between water and chloroform. The chloroform layer was dried, filtered and concentrated to give 36.4 g of crude N-(3-methylthiopropyl)glycine t-butyl ester as an oil.

Workup

  1. customAfter 5 hours the ethanol was removed on a rotary evaporator
  2. customthe residue partitioned between water and chloroform
  3. dry with materialThe chloroform layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-562d4f40adca42558e9df613c32a5a36
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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