Acetic Acid → HCID 86719580, compound

HRID 2208948Notes

Reaction equation

HRID 2208948 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([C:21]([O:23][CH3:24])=[O:22])[C:19]=1[CH3:20])[O:5][CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1.O=[C:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:28][CH2:27]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:35]([O:34][C:33]([NH:32][CH:29]1[CH2:30][CH2:31][CH:26]([NH:1][C:2]2[CH:3]=[C:4]([CH:17]=[C:18]([C:21]([O:23][CH3:24])=[O:22])[C:19]=2[CH3:20])[O:5][CH:6]2[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]2)[CH2:27][CH2:28]1)=[O:39])([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 86719579HCID 86719579, compound

Product 1

HCID 86719580HCID 86719580, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(3-amino-5-(methoxycarbonyl)-4-methylphenoxy)azetidine-1-carboxylate (0.90 g, 2.67 mmol) and tert-butyl (4-oxocyclohexyl)carbamate (0.741 g, 3.47 mmol) in dichloroethane (10 mL) was added acetic acid (0.96 g, 16.1 mmol) and the mixture stirred at room temperature for 20 minutes. Then sodium triacetoxyborohydride (1.7 g, 8.0 mmol) was added at 0° C. and the reaction 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 and the crude material purified by column chromatography to afford the title compound (0.9 g, 63%) as a mixture of cis/trans isomers.

Workup

  1. stirringthe reaction 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
  8. customthe crude material purified by column chromatography

Sources & evidence

ORD record
ord-2adfc93568e2434fa8f7114e4ef0b2e6
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…