Diethyl (cyanomethyl)phosphonate → HCID 68233453, compound

HRID 1429406Notes

Reaction equation

HRID 1429406 reaction equation
[Li+].[Cl-].P([CH2:11][C:12]#[N:13])(OCC)(OCC)=O.C1CCN2C(=NCCC2)CC1.[C:25]([O:29][C:30](=[O:42])[NH:31][C@H:32]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:33]=O)([CH3:28])([CH3:27])[CH3:26]>C(#N)C>[C:25]([O:29][C:30](=[O:42])[NH:31][C@@H:32](/[CH:33]=[CH:11]/[C:12]#[N:13])[CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 7020444tert-butyl N-[(2R)-1-oxo-3-phenylpropan-2-yl]carbamate

Product 1

HCID 68233453HCID 68233453, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of LiCl (1.0 g, 24 mmol) in dry ACN (200 mL) under nitrogen at rt, was added (EtO)2POCH2CN (4.2 g, 24 mmol), DBU (3.0 g, 20 mmol) and compound 31d (5.0 g, 20 mmol). Almost all of the salt soon dissolved and the reaction completed in 1.5 h. The reaction was quenched with citric acid, and the mixture was extracted with EA three times. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated and the residue was purified by CC (hexane/EAc=5:1) to give compound 31e (4.2 g, 77% yield).

Workup

  1. dissolutionAlmost all of the salt soon dissolved
  2. customThe reaction was quenched with citric acid
  3. extractionthe mixture was extracted with EA three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration
  7. customthe filtrate was evaporated
  8. customthe residue was purified by CC (hexane/EAc=5:1)

Sources & evidence

ORD record
ord-d5c1ecd261d34affb831c3a79948455f
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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