Diisopropylethylamine → HCID 67099598, compound

HRID 1868689Notes

Reaction equation

HRID 1868689 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:15][CH2:14][CH2:13][CH2:12]1)[C:7](=[O:16])[C:6]([C:17](OCC)=[O:18])=[C:5]2[OH:22].Cl.[C:24]([O:28][C:29](=[O:32])[CH2:30][NH2:31])([CH3:27])([CH3:26])[CH3:25].CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:12][CH2:13][CH2:14][CH2:15]1)[C:7](=[O:16])[C:6]([C:17]([NH:31][CH2:30][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:32])=[O:18])=[C:5]2[OH:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099607HCID 67099607, compound

Product 1

HCID 67099598HCID 67099598, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of ethyl 6′-chloro-4′-hydroxy-2′-oxo-spiro[cyclopentane-1,1′-naphthalen]-3′-carboxylate (0.66 g, 2 mmol) and glycine tert-butyl ester hydrochloride (0.5 g, 3 mmol) in 10 mL dioxane was treated with DIPEA (1 mL, 6 mmol). The mixture was warmed to 85° C. and stirred for 4 hours, M+1=406. The mixture was then cooled to room temperature and concentrated in vacuo. The crude product was purified by column chromatography eluting with 10-30% EtOAc hexane to give the title compound (0.8 g) as a pale yellow solid. MS (m/z)=406 (M+Na)+.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography
  4. washeluting with 10-30% EtOAc hexane

Sources & evidence

ORD record
ord-71524097648e428ca23593cd69b2e84b
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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