HCID 20027205, compound → HCID 20027171, compound

HRID 1722671Notes

Reaction equation

HRID 1722671 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH:10]([OH:27])[CH2:11][CH:12]([NH:19][C:20](=[O:26])[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH:10]([OH:27])[CH2:11][CH:12]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[NH:19][C:20](=[O:26])[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 20027205HCID 20027205, compound

Product 1

HCID 20027171HCID 20027171, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The resultant compound of Example 41 (70.0 mg, 0.161 mmol) in glacial acetic acid (15 mL) was hydrogenated over Pt black (70 mg) for 22 hours. The mixture was filtered, diluted with H2O (50 mL) and brine (50 mL), and extracted with ether (50 mL). The organic phase was washed with water (2×50 mL), saturated K2CO3 (25 mL), and brine (10 mL). Drying (MgSO4) and evaporating gave 54 mg of the desired material. Mass spectrum: (M+H)+ =441.

Workup

  1. filtrationThe mixture was filtered
  2. additiondiluted with H2O (50 mL) and brine (50 mL)
  3. extractionextracted with ether (50 mL)
  4. washThe organic phase was washed with water (2×50 mL), saturated K2CO3 (25 mL), and brine (10 mL)
  5. dry with materialDrying (MgSO4)
  6. customevaporating

Sources & evidence

ORD record
ord-8695dd410e8f4250b7c2f310164adcea
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

Loading…