Hydrochloric Acid → HCID 19789843, compound

HRID 1631866Notes

Reaction equation

HRID 1631866 reaction equation
Cl.C[NH:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8](N(CC)CC)C.[C:15]1([C:25](Cl)=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.Cl>C1COCC1>[CH3:8][O:7][C:5](=[O:6])[CH2:4][NH:3][C:25]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 701461-Naphthalenecarbonyl chloride

Product 1

HCID 19789843HCID 19789843, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methylglycinate hydrochloride (3.3 g, 26 mmol) in THF (100 mL) was added at 0° C. triethylamine (11 mL, 78 mmol). After stirring for 5 min, 1-naphthaloylchloride (4.5 mL, 31.5 mmol) was added dropwise and the resulting mixture was stirred overnight at room temperature. 10% HCl was added and the aqueous phase extracted with EtOAc. The combined organic phases were washed with 10% NaOH, brine and concentrated under vacuum. The crude compound was purified by flash chromatography using DCM/EtOAc (98:2) as eluent to give the compound 2a (5 g, 79%). 1H NMR (acetone-d6) δ 3.76 (s, 3H, OMe), 4.24 (d, J=6.0 Hz, 2H, CH2), 7.52-7.58 (m, 3H, Ar), 7.72 (dd, J=1.1 and 7.0 Hz, 1H, Ar), 7.90 (m, 1H, Ar), 8.01 (d, J=8.3 Hz, 2H, Ar), 8.46 (m, 1H, NH); 13C NMR (acetone-d6) δ 41.91 (CH2), 52.22 (OMe), 125.67, 126.07, 126.66, 127.09, 127.49, 128.99, 131.09, 131.22, 134.57, 135.36, 170.12 (CO), 171.13 (CO).

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. extractionthe aqueous phase extracted with EtOAc
  3. washThe combined organic phases were washed with 10% NaOH, brine
  4. concentrationconcentrated under vacuum
  5. customThe crude compound was purified by flash chromatography

Sources & evidence

ORD record
ord-2e607fbe3bfb4e54b47448f060a3511d
Source dataset
uspto-grants-2014_07
Patent number
US08791299B2

Reaction notes

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