4-Methylmorpholine → HCID 10901517, compound

HRID 2206348Notes

Reaction equation

HRID 2206348 reaction equation
CN1CCOCC1.C(Cl)(=O)OCC(C)C.[C:16]([NH:23][C@H:24]([C:33](O)=[O:34])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH4-].[Na+]>C(COC)OC.O>[C:19]([O:18][C:16]([NH:23][C@H:24]([CH2:33][OH:34])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid

Product 1

HCID 10901517HCID 10901517, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-Methylmorpholine (7.2 g, 72 mmol) and isobutyl chlorocarbonate (9.8 g, 72 mmol) were added to a solution of Boc-L-homophenylalanine (20 g, 72 mmol) in dimethoxyethane (100 mL) under ice-cold conditions. After one hour stirring, the reaction solution was filtered, and the filtrate was cooled in an ice bath. Thereafter, an aqueous solution (10 mL) of sodium borohydride (4.1 g, 107 mmol) was added thereto, followed by further addition of water (300 mL). The resulting precipitate was collected by filtration and washed with water and methanol to yield N-(tert-butoxycarbonyl)-L-homophenylalaninol (15 g, 79%) as a colorless crystal.

Workup

  1. filtrationthe reaction solution was filtered
  2. temperaturethe filtrate was cooled in an ice bath
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water and methanol

Sources & evidence

ORD record
ord-5648c995f84344ba9a50d094a40f0f23
Source dataset
uspto-grants-2016_06
Patent number
US09371359B2

Reaction notes

Loading…