Hydrochloric Acid → HCID 86707742, compound

HRID 1190848Notes

Reaction equation

HRID 1190848 reaction equation
[CH:1]1([NH:4][S:5]([NH:8][C@@H:9]([CH2:20][C:21]2[O:22][C:23]([CH2:26][C:27]3[S:28][C:29]4[CH:35]=[C:34]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH:33]=[CH:32][C:30]=4[N:31]=3)=[N:24][N:25]=2)[C:10]([O:12]CC2C=CC=CC=2)=O)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C[O-].[Na+].CO.Cl>C1COCC1>[CH:1]1([N:4]2[C:10](=[O:12])[C@H:9]([CH2:20][C:21]3[O:22][C:23]([CH2:26][C:27]4[S:28][C:29]5[CH:35]=[C:34]([C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=6)[CH:33]=[CH:32][C:30]=5[N:31]=4)=[N:24][N:25]=3)[NH:8][S:5]2(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 86707740HCID 86707740, compound

Product 1

HCID 86707742HCID 86707742, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Compound 181b (41 mg, 0.070 mmol) in THF (3 mL) at 0° C. was slowly added a solution of 25% NaOMe in MeOH (0.035 mL, 0.15 mmol) dissolved in THF (0.5 mL) and the mixture was stirred for 30 min. The reaction was quenched with the addition of cold 1.0 M HCl (0.70 mL, 0.70 mmol) at 0° C., then the mixture was extracted with DCM. The extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-100% EtOAc/hexanes to give Compound 181c (12 mg, 36% yield) as a yellow foam. 1H NMR (400 MHz, CDCl3) δ 8.08-8.03 (m, 2H), 7.73 (dd, J=8.6, 1.8 Hz, 1H), 7.66-7.59 (m, 2H), 7.51-7.43 (m, 2H), 7.42-7.35 (m, 1H), 4.73 (s, 2H), 4.69 (dd, J=9.0, 3.5 Hz, 1H), 3.54 (dd, J=16.8, 3.6 Hz, 1H), 3.41-3.30 (m, 1H), 2.70 (dt, J=7.1, 3.4 Hz, 1H), 1.21-1.05 (m, 2H), 1.04-0.86 (m, 2H). LCMS=1.9 min using analytical method (M), 482.0 (M+H)+.

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-f5eccb2355f6435d8e641c14a963435f
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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