Hydrochloric Acid → HCID 131711685, compound

HRID 2052265Notes

Reaction equation

HRID 2052265 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:21]([NH2:23])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].[ClH:34]>CN(C=O)C.[Pd]>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:21]([NH2:23])=[O:22])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].[ClH:34]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131711687HCID 131711687, compound

Product 1

HCID 131711685HCID 131711685, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

12.83 g (28.2 mmoles) of Z-Asp(OtBu)-D-Phg-NH2, prepared as described in Example 1, Step 3, are dissolved in 200 ml of DMF, and 2.46 ml (28.2 mmoles) of concentrated hydrochloric acid and 2 g of palladium-on-carbon catalyst are added to the cooled solution. Gaseous hydrogen is bubbled through the resulting suspension for 2.5 hours under stirring. The catalyst is filtered off, the filtrate is evaporated, the residue is dissolved in ethanol, and the solution is decolourized. Ethanol is evaporated in vacuo, and the residue is triturated with ether. 10.0 g (99%) of H-Asp(OtBu)-D-Phg-NH2.HCl are obtained; the chromatographically uniform substance melts at 169°-170° C. Rf4 =0.15.

Workup

  1. customGaseous hydrogen is bubbled through the resulting suspension for 2.5 hours
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. dissolutionthe residue is dissolved in ethanol
  5. customEthanol is evaporated in vacuo
  6. customthe residue is triturated with ether

Sources & evidence

ORD record
ord-c0f88a8ea36d4d5eb7e0d73abb58a44d
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

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