Phosphorus oxychloride → HCID 86583778, compound

HRID 844532Notes

Reaction equation

HRID 844532 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-3da6fe3465864d0185f2d22f390e1937
Source dataset
uspto-grants-2002_04
Patent number
US06380398B2

Reaction notes

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