HCID 131727676, compound → HCID 131727675, compound

HRID 1821563Notes

Reaction equation

HRID 1821563 reaction equation
[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C:4]([NH:6][C@H:7]([C:11]([N:13]1[CH2:21][CH2:20][CH2:19][C@H:14]1[C:15]([CH2:17]Cl)=[O:16])=[O:12])[CH:8]([CH3:10])[CH3:9])=[O:5])[CH3:3]>[Zn]>[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[C@H:2]([C:4]([NH:6][C@H:7]([C:11]([N:13]1[CH2:21][CH2:20][CH2:19][C@H:14]1[C:15]([CH3:17])=[O:16])=[O:12])[CH:8]([CH3:9])[CH3:10])=[O:5])[CH3:3]

Participants

3

Reactant 1

HCID 131727676HCID 131727676, compound

Product 1

HCID 131727675HCID 131727675, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

14 (1 g, 2.21 mmol) was dissolved in 5.30 ml of warm acidic acid and 1.33 g of zinc-powder was added portion wise to the stirred solution. After 24 h the remaining solid was filtered off and the filtrate was evaporated. The remaining oil was taken up in ethylacetate and washed twice with NaHCO3 and brine. The organic layer was then dried and evaporated and purified by column chromatography using a heptane/chloroform/methanol-gradient.

Workup

  1. additionwas added portion wise to the stirred solution
  2. filtrationAfter 24 h the remaining solid was filtered off
  3. customthe filtrate was evaporated
  4. washwashed twice with NaHCO3 and brine
  5. customThe organic layer was then dried
  6. customevaporated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-1d0723d658884a62a866c299975091e2
Source dataset
uspto-grants-2009_10
Patent number
US07608577B2

Reaction notes

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