Ethanol → HCID 67381738, compound

HRID 1471038Notes

Reaction equation

HRID 1471038 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[CH:11]([C:23]3[CH:40]=[CH:39][C:26]([NH:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=4[O:37][CH3:38])=[C:25]([N+:41]([O-])=O)[CH:24]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CCO.CCOC(C)=O>C1COCC1.C(Cl)Cl.O=[Pt]=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:17][CH:18]=3)[CH:11]([C:23]3[CH:24]=[C:25]([NH2:41])[C:26]([NH:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=4[O:37][CH3:38])=[CH:39][CH:40]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 67237283HCID 67237283, compound

Product 1

HCID 67381738HCID 67381738, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from example 191E (1.18 g, 1.831 mmole) was dissolved in a mixture of THF (10 mL):EtOH (10 mL):EtOAc (10 mL), treated with PtO2 (42 mg) and evacuated 10 minutes, followed by introduction of H2 (g) via balloon. The reaction mixture was stirred overnight at room temperature. The next day, the reaction mixture was filtered and the solvent removed in vacuo leaving a dark green foamy solid. The solid was dissolved in 10 mL CH2Cl2 applied to a 40 g silica gel column and eluted with a gradient of hexane/EtOAc; 90/10 to 30/70 over 20 minutes. The title compound was isolated as a white foamy solid as a mixture of isomers 0.54 g, 48%.

Workup

  1. customevacuated 10 minutes
  2. filtrationThe next day, the reaction mixture was filtered
  3. customthe solvent removed in vacuo
  4. customleaving a dark green foamy solid
  5. washeluted with a gradient of hexane/EtOAc
  6. wait90/10 to 30/70 over 20 minutes

Sources & evidence

ORD record
ord-94dfaf6e74384173b7aedaadb312e502
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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