Tert-Butylamine → [(t-Butylcarbamoyl)methyl]phosphonic acid

HRID 1390246Notes

Reaction equation

HRID 1390246 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]([CH2:9][P:10](=[O:15])([O:13]C)[O:11]C)(O)=[O:7].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]([NH:5][C:6]([CH2:9][P:10](=[O:11])([OH:15])[OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 10868DicyclohexylcarbodiimideHCID 1899642-(Dimethoxyphosphoryl)acetic acid

Product 1

HCID 22748653[(t-Butylcarbamoyl)methyl]phosphonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tertiary butyl amine (0.045 mole) and dimethyl (carboxymethyl)phosphonate (0.04 mole) were dissolved in 100 ml. of methylene chloride. As the solution was stirred, dicyclohexylcarbodiimide was added portionwise. The solution was stirred overnight and the mixture filtered. The filtrate was concentrated to a solid. It was recrystallized from an appropriate solvent such as methanol. m.p. 163°-5° C., yield, 61%.

Workup

  1. stirringThe solution was stirred overnight
  2. filtrationthe mixture filtered
  3. concentrationThe filtrate was concentrated to a solid
  4. customIt was recrystallized from an appropriate solvent such as methanol
  5. customm.p. 163°-5° C., yield

Sources & evidence

ORD record
ord-22cbed5548e44f4688d3c625e6ace161
Source dataset
uspto-grants-1979_02
Patent number
US04138432

Reaction notes

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