Triethylamine → HCID 69074467, compound

HRID 1510222Notes

Reaction equation

HRID 1510222 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[CH3:18][O:19][C:20](=[O:29])[C@@H:21]([NH2:28])[CH2:22][O:23][C:24]([CH3:27])([CH3:26])[CH3:25]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:18][O:19][C:20](=[O:29])[C@@H:21]([NH:28][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:22][O:23][C:24]([CH3:25])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 16218549Methyl O-tert-butyl-L-serinate--hydrogen chloride (1/1)

Product 1

HCID 69074467HCID 69074467, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of phenylboronic acid (1.46 g) and 4A molecular sieves (4.5 g) in dichloromethane (40 mL) were added triethylamine (1.66 mL), methyl-(2S)-2-amino-3-tert-butoxypropanoate hydrochloride (1.26 g) and copper (II) acetate (1.19 g), then the mixture was stirred at ambient temperature for 5 days. The reaction was quenched with 7N ammonia in methanol (15 mL) and the mixture was filtered through a bed of celite. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate (2:1)) to afford methyl-(2S)-2-phenylamino-3-tert-butoxypropanoate (500 mg) as a colorless syrup.

Workup

  1. customThe reaction was quenched with 7N ammonia in methanol (15 mL)
  2. filtrationthe mixture was filtered through a bed of celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate (2:1))

Sources & evidence

ORD record
ord-926cdb3403d64fc0ad7350408b39d890
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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