(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidine → (2S)-2-[1-Hydroxy-2-(4-methoxyphenoxy)ethyl]-1-[N-(phenoxy-acetyl)-L-prolyl]pyrrolidine

HRID 1720533Notes

Reaction equation

HRID 1720533 reaction equation
C(O[C:6]([N:8]1[CH2:31][CH2:30][CH2:29][C@H:9]1[C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[CH:17]([OH:28])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:11])=[O:7])(C)(C)C>Cl.O1CCOCC1>[OH:28][CH:17]([C@@H:13]1[CH2:14][CH2:15][CH2:16][N:12]1[C:10](=[O:11])[C@@H:9]1[CH2:29][CH2:30][CH2:31][N:8]1[C:6](=[O:7])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1

Participants

3

Reactant 1

HCID 22860058(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidine

Product 1

HCID 67771834(2S)-2-[1-Hydroxy-2-(4-methoxyphenoxy)ethyl]-1-[N-(phenoxy-acetyl)-L-prolyl]pyrrolidineYield 149.7%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidine (658 mg) was dissolved in 4N hydrochloric acid/1,4-dioxane (8 ml), and the mixture was stirred at room temperature for 0.5 hour. The residue obtained by concentration and drying of the reaction mixture was dissolved in methylene chloride (10 ml), and thereto were added dropwise triethylamine (0.42 ml) and phenoxyacetyl chloride (0.21 ml) under ice-cooling. After stirring the mixture under ice-cooling for 0.5 hour, and then at room temperature for 2 hours, the reaction mixture was treated in the same manner as in Example 46-D) to give 531 mg of the title compound.

Workup

  1. customThe residue obtained by concentration
  2. customdrying of the reaction mixture
  3. dissolutionwas dissolved in methylene chloride (10 ml)
  4. additionwere added dropwise triethylamine (0.42 ml) and phenoxyacetyl chloride (0.21 ml) under ice-
  5. temperaturecooling
  6. stirringAfter stirring the mixture under ice-
  7. temperaturecooling for 0.5 hour
  8. waitat room temperature for 2 hours
  9. additionthe reaction mixture was treated in the same manner as in Example 46-D)

Sources & evidence

ORD record
ord-dbc403983b034c6e8db7a6f3c8f8b519
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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