Hydrochloric Acid → HCID 70000245, compound

HRID 1264382Notes

Reaction equation

HRID 1264382 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C@@H:6]1[CH2:10][C@@H:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:8][N:7]1[S:21]([C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)(=[O:23])=[O:22].[OH-].[Na+].Cl>CCO>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][S:11][C@H:9]2[CH2:8][N:7]([S:21]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=3)(=[O:23])=[O:22])[C@H:6]([CH2:5][CH2:4][C:3]([OH:34])=[O:2])[CH2:10]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70000411HCID 70000411, compound

Product 1

HCID 70000245HCID 70000245, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

185 mg (0.37 mmol, 1eq) (2R,4R)-3-[4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-propionic acid methyl ester in 5 ml EtOH were treated with 1.85 ml 1M NaOH (1.85 mmol, 5 eq) for 2 h at RT, the pH was adjusted to 7 by the addition of 1M HCl, the solvent was evaporated and the crude product redissolved in EtOH and filtered from solids and evaporated, yielding 170 mg (94%) (2R,4R)-3-[4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-propionic acid as brown gum, MS: 486 (MH+).

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe crude product redissolved in EtOH
  3. filtrationfiltered from solids
  4. customevaporated

Sources & evidence

ORD record
ord-46c05294612149a4a6573ed3a1468609
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

Loading…