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

HRID 1651440Notes

Reaction equation

HRID 1651440 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][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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].N1CCCC1.O>C(#N)C>[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][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[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

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 13773251Benzyl 3-[N-(1-(S)-ethoxycarbonyl-3phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(R)-carboxylate

Product 1

HCID 13773252Benzyl 3-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-2,3-dihydro-5-phenyl-1,3,4-thiadiazole-2-(S)-carboxylateYield 31.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the product from step (b) (0.16g), pyrrolidine (0.16ml) and 3A molecular sieves (0.2g) in acetonitrile (3.2ml) was stirred at room temperature for 3.5 hours. The mixture was poured into water and extracted with ether, dried over magnesium sulphate and evaporated. The residue was flash chromatographed to give the sub-title product (0.05g) as a gum.

Workup

  1. extractionextracted with ether
  2. dry with materialdried over magnesium sulphate
  3. customevaporated
  4. customchromatographed

Sources & evidence

ORD record
ord-dc4d3001cae24dc29b1df23c154583a3
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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