Ammonia → HCID 9827867, compound

HRID 24059Notes

Reaction equation

HRID 24059 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:29]1[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=1)[P:13]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:21])[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:37]>CO.O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:29]1[CH:30]=[CH:31][C:32]([C:35](=[NH:37])[NH2:36])=[CH:33][CH:34]=1)[P:13]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:21])[O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 10074623Benzyl ((4-cyanophenyl)(diphenoxyphosphoryl)methyl)carbamate

Product 1

HCID 9827867HCID 9827867, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

This compound was synthesized according to (8) with slight modifications. The iminoester prepared from diphenyl [N-(benzyloxycarbonyl)amino](4-cyanophenyl)methane phosphonate (1.5 g, 3.0 mmol) was dissolved in a mixture of methanol (30 ml) and 0.5 M NH3 in 1,4-dioxane (15 ml), the solution stirred at room temperature overnight, solvent was removed and the oily residue dissolved in CHCl3 (30 ml). Diethyl ether (100 ml) was added, the precipitate collected by filtration, washed with diethyl ether (30 ml×5) and dried in vacuo [yield 1.2 g (73%)]. The crude product was judged sufficiently pure for biotinylation. For use in kinetic studies, further purification was carried out by HPLC (100 mg crude 1) yielding 36 mg 1. [tR 31.58 min, purity 99% (A:B 80:20 to 20:80 in 60 min); m/z (ESI) 516 (M+H)+, 1031 (2M+H)+].

Workup

  1. customThis compound was synthesized
  2. customsolvent was removed
  3. dissolutionthe oily residue dissolved in CHCl3 (30 ml)
  4. additionDiethyl ether (100 ml) was added
  5. filtrationthe precipitate collected by filtration
  6. washwashed with diethyl ether (30 ml×5)
  7. customdried in vacuo [yield 1.2 g (73%)]
  8. customFor use in kinetic studies, further purification

Sources & evidence

ORD record
ord-6489db67c4c940ad9747636169aa3881
Source dataset
uspto-grants-2005_02
Patent number
US06855804B2

Reaction notes

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