Triethylamine → (S)-N-(Phenylmethyl)-2-[[(S)-2-(pivaloyloxyacetyl)-1-pyrrolidinyl]carbonyl]-1-pyrrolidinecarboxamide

HRID 1735404Notes

Reaction equation

HRID 1735404 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[OH:15][CH2:16][C:17]([C@@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31]([NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])=[O:25])=[O:18].S([O-])(O)(=O)=O.[K+]>C(Cl)Cl>[C:35]1([CH2:34][NH:33][C:31]([N:27]2[CH2:28][CH2:29][CH2:30][C@H:26]2[C:24]([N:20]2[CH2:21][CH2:22][CH2:23][C@H:19]2[C:17](=[O:18])[CH2:16][O:15][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:25])=[O:32])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 178060Jtp-4819HCID 516920Potassium bisulfate

Product 1

HCID 15389025(S)-N-(Phenylmethyl)-2-[[(S)-2-(pivaloyloxyacetyl)-1-pyrrolidinyl]carbonyl]-1-pyrrolidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.59 ml), pivaloyl chloride (0.43 ml) were added, under ice-cooling, to a methylene chloride solution (25 ml) of (S)-2-[[(S)-2-(hydroxyacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (1.26 g) obtained in Example 5 and the mixture was stirred for 17 hours. The reaction mixture was poured into 5% potassium hydrogensulfate and extracted with methylene chloride. The extract was washed with saturated sodium hydrogencarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to give the title compound (1.21 g) (see Table 1).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with saturated sodium hydrogencarbonate and water in order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

Sources & evidence

ORD record
ord-7d465bad36c84b768b8f1522c0f5e890
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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