HCID 86716476, compound → HCID 2205350, compound

HRID 2275429Notes

Reaction equation

HRID 2275429 reaction equation
[CH2:1]([NH:5][C:6](=[O:33])[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])[CH2:2][CH2:3][CH3:4]>C1COCC1>[CH2:1]([NH:5][C:6](=[O:33])[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[O:8])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 86716476HCID 86716476, compound

Product 1

HCID 2205350HCID 2205350, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N1-n-butyl-N2-(5-(tert-butyldiphenylsilyloxy)pentyl)oxalamide (65 mg, 0.14 mmol) and n-tetrabutylammonium fluoride (0.41 mL, 1M soln, 0.42 mmol) in dry THF solution was stirred at room temperature under an argon atmosphere for 12 h. All volatiles were evaporated in vacuo, the residue was dissolved in EtOAc (30 mL) and the organic layer was washed with water (10 mL), brine (15 mL), dried and evaporated. Purification of the residue via SiO2 column chromatography using EtOAc/hexanes (1:2) as eluent gave the title compound (30 mg, 92%) as a colorless solid, mp 136-137° C. TLC: 50% EtOAc/hexane, Rf˜0.28; 1H NMR (300 MHz) δ 7.65 (br s, NH, 1H), 7.60 (br s, —NH, 1H), 3.65 (t, J=6.0 Hz, 2H), 3.35-3.25 (m, 4H), 1.90 (br s —OH, 1H), 1.60-1.50 (m, 6H), 1.40-1.35 (m, 4H), 0.92 (t, J=7.3 Hz, 3H); 13C NMR (100 MHz) δ 160.25, 160.10, 62.70, 39.80, 39.65, 32.40, 31.45, 29.20, 23.25, 20.20, 13.85. HRMS calcd for C11H23N2O3 [M+1]+ 231.1709. found 231.1701.

Workup

  1. customAll volatiles were evaporated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (30 mL)
  3. washthe organic layer was washed with water (10 mL), brine (15 mL)
  4. customdried
  5. customevaporated
  6. customPurification of the residue via SiO2 column chromatography

Sources & evidence

ORD record
ord-7908ed3be7364b599331e1b48f4161b1
Source dataset
uspto-grants-2015_09
Patent number
US09127027B2

Reaction notes

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