Oxalyl chloride → Benzyl cis-4-(methoxy(methyl)carbamoyl)cyclohexylcarbamate

HRID 1432414Notes

Reaction equation

HRID 1432414 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]([NH:17][CH:18]1[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH3:28][NH:29][O:30][CH3:31]>ClCCl.N1C=CC=CC=1>[CH2:7]([O:14][C:15](=[O:16])[NH:17][CH:18]1[CH2:19][CH2:20][CH:21]([C:24](=[O:26])[N:29]([O:30][CH3:31])[CH3:28])[CH2:22][CH2:23]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2852474-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acid

Product 1

HCID 86603962Benzyl cis-4-(methoxy(methyl)carbamoyl)cyclohexylcarbamateYield 38%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.796 mL, 9.1 mmol) was added slowly to a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid (2.3 g, 8.3 mmil) in dichloromethane (20 mL). The mixture was stirred at room temperature under nitrogen for 1 hour. Solvent was removed under reduced pressure. N,O-Dimethylhydroxylamine hydrochloride (0.971 g, 9.96 mmol) in anhydrous pyridine (10 mL) was added to the reaction residue. The mixture was stirred at room temperature for 3 hours. Solvent was removed under reduced pressure, and the residue was partitioned between ethyl acetate and water. Ethyl acetate solution was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 1.0 g (38%) of (4-(methoxy-methyl-carbamoyl)-cyclohexyl)-carbamic acid benzyl ester as yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.36 (m, 5H), 4.59 (s, 2H), 3.88 (m, 1H), 3.70 (s, 3H), 3.17 (s, 3H), 2.76 (m, 1H), 1.86 (m, 2H), 1.66 (m, 6H).

Workup

  1. customSolvent was removed under reduced pressure
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. customSolvent was removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. washEthyl acetate solution was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c6db49a2e97544698a3fb4f9932a8448
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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