Acetic Acid → HCID 91091752, compound

HRID 643073Notes

Reaction equation

HRID 643073 reaction equation
[CH2:1]([C@H:8]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C@@H:9]([OH:32])[CH2:10][N:11]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:12][C:13](=[O:24])[C@@H:14]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C@@H:15]([CH3:18])[CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:42](O)(=[O:44])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)C1C=CC(OC)=CC=1>CO.ClC(Cl)C.[OH-].[OH-].[Pd+2]>[CH2:1]([C@H:8]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[C@@H:9]([OH:32])[CH2:10][N:11]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:44][CH3:42])=[CH:30][CH:31]=1)[NH:12][C:13](=[O:24])[C@@H:14]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C@@H:15]([CH3:18])[CH2:16][CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 91506378HCID 91506378, compound

Product 1

HCID 91091752HCID 91091752, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 26B (1.2 g, 2.2 mmol) in methanol (7 mL) was treated with Pd(OH)2 (0.24 g), 4N HCl (0.54 mL), stirred under a hydrogen balloon at 25° C. for 16 hrs. The catalyst was filtered, washed with methanol, and the solvents were evaporated to give 1 g (100%) of the crude product used directly for the next step. This material (0.5 g, 1.1 mmol) was dissolved in dichloroethane (4 mL) and treated with acetic acid (0.12 mL, 2 equivalent), sodium triacetoxyborohydride (0.57 g, 2.5 equivalent), and p-anisaldehyde (0.26 mL, 2 equivalents) at 25° C. for 16 hrs. The mixture was quenched with 10% sodium bicarbonate and chloroform. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and the solvents were evaporated. The crude residue was purified using 1% methanol/chloroform to give 0.38 g (60%) of the title compound.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. customthe solvents were evaporated
  4. customto give 1 g (100%) of the crude product
  5. customThe mixture was quenched with 10% sodium bicarbonate and chloroform
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvents were evaporated
  11. customThe crude residue was purified

Sources & evidence

ORD record
ord-1b52d51d29dc4c25ab84aa4c502ce6bd
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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