HCID 13773263, compound → 1,3,4-Thiadiazole-2-carboxylic acid, 3-[6-amino-2-[(1-carboxy-3-phenylpropyl)amino]-1-oxohexyl]-5-(1,1-dimethylethyl)-2,3-dihydro-, [2S-[2R*,3[R*(R*)]]]-

HRID 1651447Notes

Reaction equation

HRID 1651447 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:37]([N:39]1[N:43]=[C:42]([C:44]([CH3:47])([CH3:46])[CH3:45])[S:41][C@H:40]1[C:48]([O:50]CC1C=CC=CC=1)=[O:49])=[O:38])[NH:17][C@H:18]([C:27]([O:29]CC1C=CC=CC=1)=[O:28])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:44]([C:42]1[S:41][C@@H:40]([C:48]([OH:50])=[O:49])[N:39]([C:37](=[O:38])[C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH2:11])[NH:17][C@H:18]([C:27]([OH:29])=[O:28])[CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:43]=1)([CH3:47])([CH3:45])[CH3:46]

Participants

5

Reactant 2

HCID 13773263HCID 13773263, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 137732661,3,4-Thiadiazole-2-carboxylic acid, 3-[6-amino-2-[(1-carboxy-3-phenylpropyl)amino]-1-oxohexyl]-5-(1,1-dimethylethyl)-2,3-dihydro-, [2S-[2R*,3[R*(R*)]]]-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product from step d) (1.lg) in ethanol (90ml) was treated with 10% palladium on carbon (0.9g) and the mixture stirred under 1 atmosphere of hydrogen for 1 hour. The catalyst was removed by filtration and the filtrate evaporated. The residue was recrystallised from a mixture of tetrahydrofuran and ethanol to give the title product as a white solid (0.24g)

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. customThe residue was recrystallised from a mixture of tetrahydrofuran and ethanol

Sources & evidence

ORD record
ord-2b93a0fb6d284710bcd76da1d6e8fa27
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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