HCID 58670155, compound → HCID 21101990, compound

HRID 1353170Notes

Reaction equation

HRID 1353170 reaction equation
[N:1]([CH2:4][C@H:5]1[O:9][C:8](=[O:10])[C@@H:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:6]1)=[N+]=[N-]>CO>[OH:9][CH:5]1[CH2:4][NH:1][C:8](=[O:10])[CH:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:6]1

Participants

3

Reactant 1

HCID 58670155HCID 58670155, compound

Product 1

HCID 21101990HCID 21101990, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred, argon-purged solution of compound 1B, (7.20 g, 28.1 mmol) in 150 mL of methanol at room temperature was added 10% Pd-on-carbon (1.0 g). The reaction mixture was purged, evacuated twice with argon and stirred under a hydrogen balloon near atmospheric pressure for 4 h. The slurry was purged with argon, filtered through a 0.45μ nylon filter and the filtrate evaporated to give the title compound (6.07 gm, 94%) as a gray solid, 95:5 diastereomeric mixture by HPLC. MS [M+Na]+: found 253.

Workup

  1. customThe reaction mixture was purged
  2. customevacuated twice with argon
  3. customThe slurry was purged with argon
  4. filtrationfiltered through a 0.45μ nylon
  5. filtrationfilter
  6. customthe filtrate evaporated

Sources & evidence

ORD record
ord-9b272707ccba4dc0b6776eaa4278702c
Source dataset
uspto-grants-2007_05
Patent number
US07220859B2

Reaction notes

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