Hydrochloric Acid → (S)-2-[[(S)-2-[(p-Methoxyphenoxy)acetyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

HRID 1735399Notes

Reaction equation

HRID 1735399 reaction equation
[OH:1][CH:2]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:19])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl>C(Cl)Cl.CS(C)=O>[CH3:12][O:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([C@@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[O:19])=[O:1])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14812Phosphorus oxide (P4O10)HCID 57083169(S)-2-[[(S)-2-[1-Hydroxy-2-(p-methoxyphenoxy)ethyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

Product 1

HCID 53792896(S)-2-[[(S)-2-[(p-Methoxyphenoxy)acetyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamideYield 76.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-18 °C

Procedure

(S)-2-[[(S)-2-[1-Hydroxy-2-(p-methoxyphenoxy)ethyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (5.00 g) was dissolved in methylene chloride (40 ml) and DMSO (20 ml). The mixture was cooled to -18° C. and added with diphosphorus pentaoxide (6.09 g). After stirring for 90 minutes, the reaction mixture was poured into 1.5N aqueous solution of hydrochloric acid and extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was dissolved in ethyl acetate and the mixture was left standing at room temperature for a day to give the title compound (3.83 g).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate and water in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. waitthe mixture was left
  7. waitstanding at room temperature for a day

Sources & evidence

ORD record
ord-d1e0797fc54644a3b595f046bedb64e9
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

Loading…