Acetic Acid → HCID 70873948, compound

HRID 2208949Notes

Reaction equation

HRID 2208949 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]2[CH:17]=[C:18]([CH:31]=[C:32]([C:35]([O:37][CH3:38])=[O:36])[C:33]=2[CH3:34])[O:19][CH:20]2[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:39](=O)[CH3:40].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[CH2:10][CH2:11][CH:12]([N:15]([CH2:39][CH3:40])[C:16]2[CH:17]=[C:18]([CH:31]=[C:32]([C:35]([O:37][CH3:38])=[O:36])[C:33]=2[CH3:34])[O:19][CH:20]2[CH2:21][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[CH2:23]2)[CH2:13][CH2:14]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86719580HCID 86719580, compound

Product 1

HCID 70873948HCID 70873948, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(3-((4-((tert-butoxycarbonyl)amino)cyclohexyl)amino)-5-(methoxycarbonyl)-4-methylphenoxy)azetidine-1-carboxylate (0.90 g, 1.69 mmol) and acetaldehyde (0.22 g, 5.06 mmol) in dichloroethane (10 mL), was added acetic acid (0.61 g, 10 mmol) and the reaction stirred at room temperature for 20 minutes. Then sodium triacetoxyborohydride (1.07 g, 5.05 mmol) was added at 0° C. and the reaction was stirred at room temperature for 2 h. On completion, 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 giving the title compound which was used without further purification (0.85 g).

Workup

  1. stirringthe reaction was stirred at room temperature for 2 h
  2. customOn completion, the 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

Sources & evidence

ORD record
ord-23a8eccba3d74a9d9686e9c2bdd49833
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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