Hydrochloric Acid → HCID 70386019, compound

HRID 476990Notes

Reaction equation

HRID 476990 reaction equation
C([O-])(=O)/C=C\C([O-])=O.C[O:10][C:11](=[O:35])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:34])[C@H:18]([CH3:33])[NH:19][C@H:20]([C:28]([O:30]CC)=[O:29])[CH2:21][S:22][CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-].[Na+].Cl>C(O)C>[C:28]([C@@H:20]([NH:19][C@H:18]([C:17]([N:13]1[CH2:14][CH2:15][CH2:16][C@H:12]1[C:11]([OH:35])=[O:10])=[O:34])[CH3:33])[CH2:21][S:22][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1)([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5288227Maleate(2-)HCID 70386413HCID 70386413, compound

Product 1

HCID 70386019HCID 70386019, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 300 mg portion of maleate of β-isomer of N-[(R)-1-ethoxycarbonyl-2-cyclopentylthioethyl]-alanyl-(S)-proline methyl ester prepared in Example 57 was dissolved in 2 ml of ethanol. To the solution was added dropwise 2.9 ml of 1N-NaOH at room temperature. The mixture was stirred overnight and neutralized with 2N-HCl with ice cooling. The solvent was completely removed by distillation. The residue was dissolved in methanol and the solution was subjected to high performance liquid chromatography (column=Chemcosorb 7-ODS-H, eluent=a 50:50:0.4 mixture of methanol, water and acetic acid) for separation. The solvent was distilled off. After addition of 4 ml of ether, the precipitated crystals were collected by filtration, giving the title compound as white crystals. Yield 160 mg.

Workup

  1. customThe solvent was completely removed by distillation
  2. dissolutionThe residue was dissolved in methanol
  3. additiona 50:50:0.4 mixture of methanol, water and acetic acid)
  4. customfor separation
  5. distillationThe solvent was distilled off
  6. additionAfter addition of 4 ml of ether
  7. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-073f08d1faaf4c9590a23c354d1a09d1
Source dataset
uspto-grants-1989_12
Patent number
US04886813

Reaction notes

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