Diisopropylethylamine → HCID 67099775, compound

HRID 2078329Notes

Reaction equation

HRID 2078329 reaction equation
[OH:1][C:2]1[C:3]2[CH:4]=[CH:5][N:6]=[CH:7][C:8]=2[C:9]([CH3:19])([CH3:18])[C:10](=[O:17])[C:11]=1[C:12]([O:14]CC)=O.Cl.[NH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(N(C(C)C)C(C)C)C>O1CCOCC1.O.CCOC(C)=O>[OH:1][C:2]1[C:3]2[CH:4]=[CH:5][N:6]=[CH:7][C:8]=2[C:9]([CH3:18])([CH3:19])[C:10](=[O:17])[C:11]=1[C:12]([NH:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:14]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67100075HCID 67100075, compound

Product 1

HCID 67099775HCID 67099775, compoundYield 7.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 5-hydroxy-8,8-dimethyl-7-oxo-7,8-dihydroisoquinoline-6-carboxylate (0.2 g, 0.8 mmol) and tert-butyl 2-aminoacetate hydrochloride (0.2 g, 0.9 mmol) in 1 mL dioxane was treated with N-ethyl-N-isopropylpropan-2-amine (0.4 mL, 2 mmol). The mixture was warmed to 100° C. and stirred for 2.5 hours, M+1=347. The mixture was cooled to room temperature, diluted with 20 mL H2O, and 100 mL EtOAc. The organic layer was concentrated. The crude product was purified by column eluting with 10-20% EtOAc/hexane to give 0.02 g of the product as an off-white solid. MS m/e: (M+H)+ 347.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationThe organic layer was concentrated
  3. customThe crude product was purified by column
  4. washeluting with 10-20% EtOAc/hexane

Sources & evidence

ORD record
ord-374bbf867850477ba88c7f5f284d3657
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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