Benzyl 3-[N-(1-(S)-ethoxycarbonyl-3phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(R)-carboxylate → 3-[N-(1-(S)-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(R)-carboxylic acid

HRID 1651442Notes

Reaction equation

HRID 1651442 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:20]1[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:22][C@@H:21]1[C:31]([O:33]CC1C=CC=CC=1)=[O:32])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:20]1[N:24]=[C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[S:22][C@@H:21]1[C:31]([OH:33])=[O:32])=[O:19])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 13773251Benzyl 3-[N-(1-(S)-ethoxycarbonyl-3phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(R)-carboxylate

Product 1

HCID 137732553-[N-(1-(S)-Ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(R)-carboxylic acidYield 52.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product from Example 1, step (b) (0.43g) in ethanol (100ml) was treated with 10% palladium on charcoal (0.lg) and stirred in a pressure vessel under hydrogen at 3 atmospheres at room temperature for 3 days. The catalyst was filtered off and the filtrate evaporated. The residue was triturated with a mixture of ether and petroleum ether (bp 40°-60°) to give the title product (0.19g) as a pale grey, non-crystalline solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customThe residue was triturated with a mixture of ether and petroleum ether (bp 40°-60°)

Sources & evidence

ORD record
ord-afbb03e33e9c4b5fab115d3abd179cd3
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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