HCID 89427988, compound → HCID 67402855, compound

HRID 2204981Notes

Reaction equation

HRID 2204981 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][S:21][CH2:22][C@H:23]([N:28]=[N+]=[N-])[CH2:24][N:25]=[N+]=[N-])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.[OH-].[OH-].[Pd+2]>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][S:21][CH2:22][C@H:23]([NH2:28])[CH2:24][NH2:25])[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 89427988HCID 89427988, compound

Product 1

HCID 67402855HCID 67402855, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-diazidopropylthio)propanoate (1 eq) was stirred in dry EtOH (0.05 M) under nitrogen at room temperature. Pd(OH)2 (0.5 eq) was then added in one portion. The reaction was purged with, then stirred under hydrogen atmosphere (1 atm) for 16 hours at room temperature. The crude material was then filtered twice through celite and cotton. The organics were concentrated and used in the next step without further purification.

Workup

  1. customThe reaction was purged with,
  2. filtrationThe crude material was then filtered twice through celite and cotton
  3. concentrationThe organics were concentrated
  4. customused in the next step without further purification

Sources & evidence

ORD record
ord-ee427b0b70d24d5aa161ab1468c00402
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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