Triethylamine → HCID 13857262, compound

HRID 2171268Notes

Reaction equation

HRID 2171268 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][C@H:15]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH:17]([CH3:19])[CH3:18].C(=O)([O-])O.[Na+]>C1COCC1>[CH3:8][S:9]([O:13][CH2:14][C@H:15]([NH:20][C:21]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:27])[CH2:16][CH:17]([CH3:19])[CH3:18])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 16211316tert-Butyl [(2R)-1-hydroxy-4-methylpentan-2-yl]carbamate

Product 1

HCID 13857262HCID 13857262, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (59 ml) and methanesulfonylchloride (25 ml) were added to a THF solution (200 ml) containing (R)-tert-butyl (1-hydroxy-4-methylpentan-2-yl)carbamate (46.2 g) in an ice bath, followed by stirring for 0.5 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure. A white solid of (R)-2-((tert-butoxycarbonyl)amino)-4-methylpentyl methanesulfonate (60 g) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-e7692659b9a44215993fe8c5ed92f90e
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

Loading…