Hydrochloric Acid → HCID 54224371, compound

HRID 1735409Notes

Reaction equation

HRID 1735409 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][CH2:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([C@@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])=[O:11].Cl>N1C=CC=CC=1>[C:1]([O:8][CH2:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([C@@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 54137523HCID 54137523, compound

Product 1

HCID 54224371HCID 54224371, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.42 ml) was added, under ice-cooling, to a pyridine solution (2.4 ml) of (S)-2-[[(S)-2-(hydroxyacetyl)1-pyrrolidinyl]carbonyl]-1-octanoylpyrrolidine (1.06 g) obtained in Example 14 and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into 1% hydrochloric acid and extracted with ethyl acetate. The extract was washed with 1% hydrochloric acid, water, 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 (1.02 g) (see Table 4).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 1% hydrochloric acid, water, 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-6bd65fef60f649fdbb2e830dbafae617
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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