Phosphorus oxychloride → HCID 86583778, compound

HRID 479619Notes

Reaction equation

HRID 479619 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([C:13]([N:15]1[CH2:19][CH:18]=[CH:17][C@H:16]1[C:20](=O)[NH2:21])=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([C:13]([N:15]1[CH2:19][CH:18]=[CH:17][C@H:16]1[C:20]#[N:21])=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86583779HCID 86583779, compound

Product 1

HCID 86583778HCID 86583778, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

(175 mg, 0.54 mmol) of (2) was dissolved in 4 ml of pyridine and the mixture was cooled to 0° C. Phosphorus oxychloride (0.2 ml, 2.15 mmol) was added dropwise and after 10 minutes of stirring the reaction mixture was poured into 20 ml of ice water and the organic material was extracted into 5×10 ml of ethyl acetate. The combined organic extract was washed with 2×20 ml of water, 1×20 ml of brine and dried over magnesium sulphate. The solvent was evaporated to afford 140 mg of (S,S) [1-(2-Cyano-2,5-dihydro-pyrrole-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester (3). Oil, 85% yield. 1H-NMR (CDCl3, 200 MHz) δ: 1.05 (s, 9H); 1.42 (s, 9H); 4.22 (d, 1H); 4.39-4.53 (m, 1H); 4.65-4.77 (m, 1H); 5.30 (d, 1H); 5.41-5.48 (m, 1H); 5.83-5.90 (m, 1H); 6.09-6.15 (m, 1H).

Workup

  1. extractionthe organic material was extracted into 5×10 ml of ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed with 2×20 ml of water, 1×20 ml of brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-61e6304f6afc4c42ab79a142393e80a7
Source dataset
uspto-grants-2003_11
Patent number
US06645995B2

Reaction notes

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