HCID 86743725, compound → HCID 14674574, compound

HRID 330626Notes

Reaction equation

HRID 330626 reaction equation
C([O:8][C:9](=[O:60])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:59])[C@H:16]([CH2:44][CH2:45][CH2:46][CH2:47][NH:48]C(OCC1C=CC=CC=1)=O)[NH:17][C@H:18]([C:39]([O:41]CC)=[O:40])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]1[CH2:28][CH2:27][N:26](C(OCC2C=CC=CC=2)=O)[CH2:25][CH2:24]1)C1C=CC=CC=1>CO.[Pd]>[C:39]([C@@H:18]([NH:17][C@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:60])=[O:8])=[O:59])[CH2:44][CH2:45][CH2:46][CH2:47][NH2:48])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]1[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1)([OH:41])=[O:40]

Participants

4

Reactant 1

HCID 86743725HCID 86743725, compound

Product 1

HCID 14674574HCID 14674574, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The Nα -[1(S)-ethoxycarbonyl-5-(1-benzyloxycarbonyl-4-piperidyl)pentyl]-Nε -benzyloxycarbonyl-L-lysyl-L-proline benzylester obtained by Example VIII a) (1.1 g) is dissolved in methanol, and palladium black is added for catalytic reduction. After completion of reaction for 5 hours, the methanol is evaporated in vacuo. The residue is added into 10 ml of 1N-NaOH and dissolved. This solution is left standing at room temperature for 1 hour, and thereafter is treated with cation ion-exchange resin DOWEX 50W-X2. The impurities are removed with 2% pyridine. Then, the eluted fractions by aqueous 4% ammonia are subjected to freeze drying to obtain 300 mg of hygroscopic white powder (Rf=0.08, expansive solvent, B).

Workup

  1. customAfter completion of reaction for 5 hours
  2. customthe methanol is evaporated in vacuo
  3. additionThe residue is added into 10 ml of 1N-NaOH
  4. dissolutiondissolved
  5. waitThis solution is left
  6. additionis treated with cation ion-exchange resin DOWEX 50W-X2
  7. customThe impurities are removed with 2% pyridine
  8. customto freeze drying

Sources & evidence

ORD record
ord-edf20358ea584592bd91d8d5488aaa76
Source dataset
uspto-grants-1990_01
Patent number
US04897483

Reaction notes

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