Acetic Acid → HCID 57635641, compound

HRID 535972Notes

Reaction equation

HRID 535972 reaction equation
[C:1]1([C:7]2[N:11]3[CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:10]3=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1COCC1>[CH3:24][N:15]1[CH2:14][CH2:13][CH2:12][N:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:10]2[CH2:16]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57635680HCID 57635680, compound

Product 1

HCID 57635641HCID 57635641, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of intermediate 64A (0.91 g, 3.17 mmol) in 20 mL THF was added formaldehyde (37% in water, 2.36 mL) followed by sodium triacetoxyborohydride (1.34 g, 6.34 mmol) and acetic acid (0.27 mL, 4.76 mmol). The resulting mixture was stirred at room temperature overnight and then quenched with NaHCO3 saturated solution and stirred for 10 minutes. The reaction mixture was concentrated under vacuum and extracted with 10% iPrOH/DCM.

Workup

  1. customquenched with NaHCO3 saturated solution
  2. stirringstirred for 10 minutes
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. extractionextracted with 10% iPrOH/DCM

Sources & evidence

ORD record
ord-201e7389d5b245b2ad5dac4098b9642f
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

Loading…