Tetrahydrofuran → HCID 53248102, compound

HRID 2174455Notes

Reaction equation

HRID 2174455 reaction equation
[N:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]([O:9][CH3:10])=[O:8])=[N+:2]=[N-:3].[S:11]1C=CC=C1CC(O)=O.CCN(C(C)C)C(C)C.C1C[O:32][CH2:31][CH2:30]1>>[C:31]([S:11][CH:5]([CH2:4][N:1]=[N+:2]=[N-:3])[CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:32])[CH3:30]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 159702-Thiopheneacetic acidHCID 81531DiisopropylethylamineHCID 10749271HCID 10749271, compound

Product 1

HCID 53248102HCID 53248102, compoundYield 81%

Conditions

Temperature
0 °C

Procedure

To the solution of (E)-Methyl 4-azidobut-2-enoate (4.00 g, 28.37 mmol) in 60 ml of THF at 0° C. was added the mixture of thiolacetic acid (3.0 ml, 42.09 mmol) and DIPEA (8.0 ml, 45.92 mmol) in 60 ml of THF in 20 min. After stirred at 0° C. for 1 hr, the mixture was stirred at RT overnight, evaporated, redissolved in CH2Cl2, washed with NaHCO3 (sat.) and 1 M NaH2PO4/NaCl (sat.), pH 4 respectively, dried over MgSO4, filtered, evaporated and chromatographic purification on SiO2 column eluted with EtAc/Hexane (1:8 to 1:4) to afford HRMS for 4.98 g (81%) of the title product. 1H NMR (CDCl3) 3.66 (m, 1H), 3.62 (s, 3H), 3.40 (dd, 1H, J=7.5, 12.7 Hz), 3.31 (m, 1H), 2.78 (m, 1H), 2.60 (m, 1H), 2.32 (s, 3H); 13C NMR (DMF-d7) 192.20, 172.48, 56.56, 53.60, 51.31, 34.58, 30.56; ESI MS m/z+240.0 (M+Na), 255.9 (M+K); HRMS m/z+(C7H11N3O3S+Na) calcd 240.0419. found 240.0415.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customevaporated
  3. dissolutionredissolved in CH2Cl2
  4. washwashed with NaHCO3 (sat.) and 1 M NaH2PO4/NaCl (sat.), pH 4 respectively
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customchromatographic purification on SiO2 column
  9. washeluted with EtAc/Hexane (1:8 to 1:4)

Sources & evidence

ORD record
ord-97087d9ba74945e5929eaaa6fbcb2629
Source dataset
uspto-grants-2015_06
Patent number
US09061995B2

Reaction notes

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