HCID 71256870, compound → HCID 86700494, compound

HRID 705180Notes

Reaction equation

HRID 705180 reaction equation
[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([NH:12][C:13](=[O:31])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([B:22]4[O:26]C(C)(C)C(C)(C)[O:23]4)=[CH:18][CH:17]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]>N#N>[C:1]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([NH:12][C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([B:22]([OH:23])[OH:26])=[CH:18][CH:17]=3)=[O:31])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

3

Reactant 1

HCID 71256870HCID 71256870, compound

Product 1

HCID 86700494HCID 86700494, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 947NitrogenSolvent

Procedure

Compound 9 (61 mg, 0.14 mmol, 1 equiv.) was dissolved in N2-sparged tetrahydrofuran (THF, 10 mL) prior to addition of concentrated HCl (0.8 mL) and N2-sparged deionized water (8 mL). The reaction mixture was stirred for one hour prior to the addition of an additional 8 mL DI H2O. After 15 min, the THF was removed under vacuum, and the precipitate that formed was collected via filtration and rinsed with DI H2O. To remove residual starting material, the crude product was precipitated from diethyl ether to yield 49 mg (73%) of a white powder. 1H NMR (400 MHz, d6-Acetone): δ5.27 (2H, s), 7.22 (2H, s), 7.45 (2H, d, J=8.0 Hz), 7.80 (1H, dd, J=9.4, 2.2 Hz), 7.92 (2H, d, J=8.4 Hz), 8.17 (1H, d, J=9.6 Hz), 8.63 (1H, d, J=2.0 Hz).

Workup

  1. customsparged tetrahydrofuran (THF, 10 mL)
  2. additionto addition of concentrated HCl (0.8 mL) and N2-
  3. customsparged deionized water (8 mL)
  4. additionto the addition of an additional 8 mL DI H2O
  5. waitAfter 15 min
  6. customthe THF was removed under vacuum
  7. customthe precipitate that formed
  8. filtrationwas collected via filtration
  9. washrinsed with DI H2O
  10. customTo remove residual
  11. customthe crude product was precipitated from diethyl ether

Sources & evidence

ORD record
ord-0d3fa4ca204b4b1787c7be8fa8187b6c
Source dataset
uspto-grants-2015_11
Patent number
US09173966B2

Reaction notes

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