Hydrochloric Acid → HCID 178490233, compound

HRID 376549Notes

Reaction equation

HRID 376549 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@@H:5]1[N:10]([C:11](=[O:33])[C@@H:12]([NH:22][C:23](OCC2C=CC=CC=2)=[O:24])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:9][CH2:8][N:7]([CH2:34][C:35]([OH:37])=[O:36])[C:6]1=[O:38].C(=O)([O-])O.[Na+].O=C1N(O[C:55](=[O:66])[C:56]2[CH:61]=[CH:60][C:59]([NH:62][C:63]([NH2:65])=[NH:64])=[CH:58][CH:57]=2)C(=O)C2C1C1CC2C=C1.[ClH:69]>CO.[H][H].O1CCOCC1.O>[ClH:69].[NH:62]([C:59]1[CH:60]=[CH:61][C:56]([C:23]([NH:22][C@@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C:11]([N:10]2[CH2:9][CH2:8][N:7]([CH2:34][C:35]([OH:37])=[O:36])[C:6](=[O:38])[C@@H:5]2[CH2:4][CH2:3][CH2:2][NH:1][C:55](=[O:66])[C:56]2[CH:57]=[CH:58][C:59]([NH:62][C:63]([NH2:65])=[NH:64])=[CH:60][CH:61]=2)=[O:33])=[O:24])=[CH:57][CH:58]=1)[C:63]([NH2:65])=[NH:64]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 54085635HCID 54085635, compoundHCID 178512549HCID 178512549, compound

Product 1

HCID 178490233HCID 178490233, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

In 5 ml of methanol was dissolved 250 mg of (S,S)-3-(3-aminopropyl)-4-[2-benzyloxycarbonylamino-3-(4-methoxyphenyl)propionyl]-2-oxopiperazine-1-acetic acid produced in Reference Example 36. To the solution was added 100 mg of 10% Pd--C, and the mixture was stirred for one hour at room temperature in hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to leave an oily substance. The oily substance was dissolved in a mixture of 10 ml of dioxane and 10 ml of water. To the solution were added 210 mg of sodium hydrogencarbonate and 450 mg of 4-guanidinobenzoic acid 3,5-dioxo-4-azatricyclo[5,2,1,0 2,6]deca-8-en-4-ylester. The mixture was stirred for one hour at room temperature. The pH of the reaction mixture was adjusted to 3 with 1N HCl, then dioxane was distilled off under reduced pressure. The remaining aqueous solution was subjected to a CHP-20 column. The fraction eluted with 10% acetonitrile/water was freeze-dried to afford 130 mg of the title compound as an amorphous powdery product.

Workup

  1. customproduced in Reference Example 36
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto leave an oily substance
  5. distillationdioxane was distilled off under reduced pressure
  6. washThe fraction eluted with 10% acetonitrile/water
  7. customwas freeze-dried

Sources & evidence

ORD record
ord-53e1c61ccf5c42a7aa8197a14a72c8f1
Source dataset
uspto-grants-2000_02
Patent number
US06020334

Reaction notes

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