Diisopropylethylamine → HCID 67099631, compound

HRID 1868699Notes

Reaction equation

HRID 1868699 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH3:20])([CH3:19])[C:5](=[O:18])[C:6]([C:13](OCC)=[O:14])=[C:7]2[OH:12].C(N(C(C)C)C(C)C)C.Cl.[NH2:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>O1CCOCC1>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH3:19])([CH3:20])[C:5](=[O:18])[C:6]([C:13]([NH:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:14])=[C:7]2[OH:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099633HCID 67099633, compound

Product 1

HCID 67099631HCID 67099631, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 5-fluoro-1-hydroxy-4,4-dimethyl-3-oxo-3,4-dihydronaphthalene-2-carboxylate (2.0 g, 7.2 mmol) in 1,4-dioxane (15 mL), was added N-ethyl-N-isopropylpropan-2-amine (2.3 mL, 13 mmol) and tert-butyl 2-aminoacetate hydrochloride (1.6 g, 9.3 mmol). After heating at 80° C. for 12 hours, the solvent was removed in vacuo, and the residue was purified using flash chromatography (15% EtOAc/hexane) to afford the product as a white solid (1.6 g). MS (m/z)=362 (M+H)+.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-776dba3e12e54fa68e88cf6042d06888
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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