HCID 86716476, compound → HCID 2205350, compound

HRID 1485812Notes

Reaction equation

HRID 1485812 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, 1 M 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-e647f49fb23248fc9cdc0f090ff81afd
Source dataset
uspto-grants-2016_08
Patent number
US09422318B2

Reaction notes

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