Isobutyl chloroformate → HCID 178462117, compound

HRID 1944712Notes

Reaction equation

HRID 1944712 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.[C:26]1([C@H:32]([NH2:34])[CH3:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.C(N(CC)CC)C>[C:26]1([C@H:32]([NH:34][C:15]([C@H:12]2[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:14][CH2:13]2)=[O:17])[CH3:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 62365Isobutyl chloroformateHCID 6431891-Phenethylamine, (+)-HCID 178453972HCID 178453972, compound

Product 1

HCID 178462117HCID 178462117, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (5 g, 20.5 mmol) was dissolved in THF, to which triethylamine (3 mL) was added. The reaction mixture was cooled to 0° C. and a solution of isobutyl chloroformate (2.8 g, 20.7 mmol) in THF was added dropwise. The resulting white suspension was stirred at room temperature for 30 min, after which a solution of (R)-1-phenylethanamine (2.9 g, 20.5 mmol) in THF was added dropwise. The reaction mixture was then stirred at room temperature for 4 h, after which LC-MS showed one major peak corresponding to desired product. The reaction mixture was concentrated, and the residue was diluted with water (250 mL). The resulting white precipitate was filtered, washing with ether, to afford a dry white solid tert-butyl trans-4-((R)-1-phenylethylcarbamoyl)cyclohexylcarbamate (5.2 g).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was then stirred at room temperature for 4 h

Sources & evidence

ORD record
ord-4abcc8f9aef84b2a987e264251fd4f00
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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