Acetic Acid → HCID 69560775, compound

HRID 2299010Notes

Reaction equation

HRID 2299010 reaction equation
[CH2:1]([CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]=[CH:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[CH:21]=[C:20]([C:25]#[N:26])[CH:19]=[CH:18]4)[CH:11]=2)[CH2:6][NH:5][CH2:4]1)[CH3:2].[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH2:27]([N:5]1[CH2:4][CH:3]([CH2:1][CH3:2])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]=[CH:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[CH:21]=[C:20]([C:25]#[N:26])[CH:19]=[CH:18]4)[CH:11]=2)[CH2:6]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69562198HCID 69562198, compound

Product 1

HCID 69560775HCID 69560775, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 49A (600 mg) in dichloromethane (25 mL) was treated sequentially with benzaldehyde (0.7 mL), sodium triacetoxyborohydride (1.3 g), and acetic acid (319 mg), stirred for 24 hours, diluted with dichloromethane, washed with 1M NaOH and brine, dried (MgSO4), filtered, and concentrated. The concentrate was crystallized from diethyl ether/hexanes to provide the desired product.

Workup

  1. washwashed with 1M NaOH and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was crystallized from diethyl ether/hexanes

Sources & evidence

ORD record
ord-6c097ffeaaa94cdda5fc6ac1463f38d7
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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