Hydrochloric Acid → HCID 90052423, compound

HRID 2284781Notes

Reaction equation

HRID 2284781 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([OH:17])=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:25]1[CH:29]=CN=C1)(N1C=CN=C1)=O.C(N(CC)C(C)C)(C)C.Cl.[CH3:40][O:41]N.Cl>C(Cl)Cl>[CH3:40][O:41][N:25]([CH3:29])[C:15]([C@@H:11]1[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10]1)=[O:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 16218560CYCLOHEXANECARBOXYLIC ACID, 3-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-, (1R,3S)-

Product 1

HCID 90052423HCID 90052423, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1R*,3S*)-3-((tert-butoxycarbonyl)amino)cyclohexanecarboxylic acid (M1, 3.00 g) as racemate synthesized according to the method described in Chemistry A European Journal, 2005, 11, pp. 6543-6551 in methylene chloride (30 mL), carbonyldiimidazole (2.60 g) was added under ice cooling, and the mixture was stirred at the same temperature for 10 minutes. To the reaction mixture, N,N-diisopropylethylamine (2.72 mL) and methoxyamine hydrochloride (1.56 g) were added under ice cooling, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 1.0 mol/L aqueous hydrochloric acid and methylene chloride were added. The organic layer was separated, and the aqueous layer was extracted with methylene chloride. The organic layer and the extract were combined, washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain oily tert-butyl ((1S*,3R*)-3-(methoxy(methyl)carbamoyl)cyclohexyl)carbamate (M2, 3.60 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. washwashed successively with water, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-218e545ab3f444e49df4aaf5ed6db88b
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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