Triethylamine → HCID 69188199, compound

HRID 885508Notes

Reaction equation

HRID 885508 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([NH2:17])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH3:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[C:24]([CH3:27])[C:25]=1[F:26].C(N(CC)CC)C>ClCCl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3](=[O:18])[C@H:4]([NH:17][C:22]1[CH:23]=[C:24]([CH3:27])[C:25]([F:26])=[C:20]([CH3:19])[CH:21]=1)[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13645075(R)-Methyl 2-amino-6-((tert-butoxycarbonyl)amino)hexanoateHCID 17750045(4-Fluoro-3,5-dimethylphenyl)boronic acid

Product 1

HCID 69188199HCID 69188199, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-2-Amino-6-tert-butoxycarbonylamino-hexanoic acid methyl ester (3.000 g, 10.108 mmol), 3,5-dimethyl-4-fluorophenylboronic acid (3.398 g, 20.216 mmol), Cu(OAc)2 (2.019 g, 11.119 mmol), and molecular sieves 4 Å (7.591 g) in 45 mL of dichloromethane, was added triethylamine (2.8 mL, 20.216 mmol). After stirring at room temperature under O2 (1 atm) for 87 h, the reaction mixture was filtered through a pad of Celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-30% ethyl acetate/hexanes to give the title compound as colorless oil (3.084 g, 80% yield). LC-MS: tR=9.8 min; m/z 383 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe product was isolated by Flash column chromatography (silica gel column)
  5. washeluting with 0-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b5c9e6337f2d4036a402df2f9110bec7
Source dataset
uspto-grants-2012_08
Patent number
US08242174B2

Reaction notes

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