Acetic Acid → HCID 70913572, compound

HRID 2208922Notes

Reaction equation

HRID 2208922 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[C:17]([CH3:30])=[C:18]([CH:23]=[C:24]([O:26][CH2:27][CH2:28][OH:29])[CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:31](=O)[CH3:32].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]([CH2:31][CH3:32])[C:16]2[C:17]([CH3:30])=[C:18]([CH:23]=[C:24]([O:26][CH2:27][CH2:28][OH:29])[CH:25]=2)[C:19]([O:21][CH3:22])=[O:20])[CH2:11][CH2:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70874086HCID 70874086, compound

Product 1

HCID 70913572HCID 70913572, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 3-((4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-5-(2-hydroxyethoxy)-2-methylbenzoate (2.0 g, 4.7 mmol) and acetaldehyde (0.63 g, 14.2 mmol) in dichloroethane (20 mL) was added acetic acid (1.7 g, 28 mmol) and the reaction mixture stirred at room temperature for 20 minutes. Then sodium triacetoxyborohydride (3.0 g, 14.2 mmol) was added at 0° C. and reaction was stirred at room temperature for 2 h. On completion, the reaction was quenched with aqueous sodium bicarbonate, the organic phase was separated and the aqueous phase extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure; Crude material was purified by column chromatography to afford the title compound (1.9 g, 89%).

Workup

  1. customreaction
  2. stirringwas stirred at room temperature for 2 h
  3. customOn completion, the reaction was quenched with aqueous sodium bicarbonate
  4. customthe organic phase was separated
  5. extractionthe aqueous phase extracted with dichloromethane
  6. washThe combined organic layers were washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customCrude material was purified by column chromatography

Sources & evidence

ORD record
ord-a44ffacb2da64dbaa35d287fa2e2239b
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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