Diisopropylethylamine → 1,1-Dimethylethyl N-((7-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 2078157Notes

Reaction equation

HRID 2078157 reaction equation
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([OH:29])=[C:16]([C:24](OCC)=[O:25])[C:17](=[O:23])[C:18]2([CH3:22])[CH3:21])=[CH:13][CH:12]=1.Cl.[C:31]([O:35][C:36](=[O:39])[CH2:37][NH2:38])([CH3:34])([CH3:33])[CH3:32]>O1CCOCC1.CCOCC>[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([OH:29])=[C:16]([C:24]([NH:38][CH2:37][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:39])=[O:25])[C:17](=[O:23])[C:18]2([CH3:22])[CH3:21])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099815Ethyl 7-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate

Product 1

HCID 670999541,1-Dimethylethyl N-((7-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinateYield 115.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

DIPEA (0.718 mL, 4.12 mmol) was added to a mixture of ethyl 7-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (810 mg, 2.75 mmol) and glycine tert-butyl ester hydrochloride (553 mg, 3.30 mmol) in dioxane (25 mL). The reaction mixture was stirred at 85° C. for 2 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo to give a yellow solid. The crude solid was suspended in ether and filtered to give the desired ester as a white solid (1.21 g). MS (m/e)=324.1 (M+H-tBu)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto give a yellow solid
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9d4068ffaed24fadb61f1b0ec874c3b3
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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