Diisopropylethylamine → HCID 89478069, compound

HRID 1848392Notes

Reaction equation

HRID 1848392 reaction equation
[OH:1][C:2]1[C:10](=[O:11])[N:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH:17](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>CO.C(#N)C>[CH3:17][O:1][C:2]1[C:10](=[O:11])[N:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 89477712HCID 89477712, compound

Product 1

HCID 89478069HCID 89478069, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

At 0° C. to a solution of Intermediate 22C (30 mg, 0.13 mmol) and N,N-diisopropylethylamine (35 μL, 0.20 mmol) in methanol (0.15 mL) and acetonitrile (1.35 mL) was added (trimethylsilyl)diazomethane (0.10 mL, 2.0 M in diethyl ether, 0.20 mmol). The reaction mixture was stirred at rt for 2 h, concentrated and the residue was purified by ISCO chromatography (ethyl acetate/hexane 0-100%, column, 4 g) to afford Intermediate 22D (20 mg, 63%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.25-1.41 (5H, m), 1.50-1.61 (1H, m), 1.76-1.98 (2H, m), 2.44-2.52 (1H, m), 2.79-2.90 (1H, m), 3.95 (1H, dd, J=11.4, 3.6 Hz), 4.23-4.38 (6H, m).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by ISCO chromatography (ethyl acetate/hexane 0-100%, column, 4 g)

Sources & evidence

ORD record
ord-53775c38fc53428f87229022c5d853f0
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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