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

HRID 371700

Reaction equation

HRID 371700 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-fdc5e424f1ab4d7eb193b14a80ef3588
Source dataset
uspto-grants-1978_05
Patent number
US04087522

Linked notes

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