Acetic Acid → HCID 70874015, compound

HRID 2208926Notes

Reaction equation

HRID 2208926 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]([CH3:31])=[C:18]([CH:23]=[C:24]([O:26][CH2:27][CH2:28][O:29][CH3:30])[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:32](=O)[CH3:33].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]([CH2:32][CH3:33])[C:16]2[C:17]([CH3:31])=[C:18]([CH:23]=[C:24]([O:26][CH2:27][CH2:28][O:29][CH3:30])[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 70873659HCID 70873659, compound

Product 1

HCID 70874015HCID 70874015, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 3-((4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-5-(2-methoxyethoxy)-2-methylbenzoate (1.60 g, 3.67 mmol) and acetaldehyde (0.48 g, 10.9 mmol) in dichloroethane (20 mL) was added acetic acid (1.3 g, 22 mmol) and the reaction mixture stirred at room temperature for 20 minutes. Then sodium triacetoxyborohydride (2.33 g. 11.0 mmol) was added at 0° C. and the reaction was stirred at room temperature for 2 h. The reaction was quenched with aqueous sodium bicarbonate, the organic phase separated and the aqueous phase extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure, the crude material was purified by column chromatography to afford the title compound (1.6 g, 94%).

Workup

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

Sources & evidence

ORD record
ord-06d94d833ee844d1a9626d1341d23c8f
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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