HCID 178451026, compound → HCID 178451021, compound

HRID 1289256Notes

Reaction equation

HRID 1289256 reaction equation
C(OC([NH:11][C@@H:12]([C:22]1[NH:26][N:25]=[N:24][N:23]=1)[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@@H:12]([C:22]1[NH:26][N:25]=[N:24][N:23]=1)[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16]

Participants

4

Reactant 1

HCID 178451026HCID 178451026, compound

Product 1

HCID 178451021HCID 178451021, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl (4R)-4-(benzyloxycarbonylamino)-4-(tetrazol-5-yl)-butyrate (1.2 g, 3.32 mmol) in ethanol (77 ml) was stirred with 10% Pd-C (0.166 g) under a hydrogen atmosphere at ambient temperature for 16 hours. The catalyst was removed by filtration and the filtrate evaporated. Dichloromethane was added to the residue and evaporated and the resulting solid was triturated with hexane and dried to give tert-butyl (4R)-4-amino-4-(tetrazol-5-yl)butyrate (0.687 g, 91%), m.p. 175° C. (decomp.).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. additionDichloromethane was added to the residue
  4. customevaporated
  5. customthe resulting solid was triturated with hexane
  6. customdried

Sources & evidence

ORD record
ord-c51508cb4cc34c8a94fe0a217ee58be6
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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