Hydrochloric Acid → HCID 86680531, compound

HRID 1184614Notes

Reaction equation

HRID 1184614 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]2[CH2:18][C@H:19]([O:21][C:22]3[CH:27]=[N:26][C:25]([CH:28]4[CH2:30][CH2:29]4)=[CH:24][N:23]=3)[CH2:20][C@H:14]2[CH2:13]1)=[O:11])C)(C)(C)C.Cl>O1CCOCC1>[CH:28]1([C:25]2[N:26]=[CH:27][C:22]([O:21][C@H:19]3[CH2:18][N:15]4[CH2:16][CH2:17][N:12]([C:10](=[O:11])[C@H:9]([NH:7][CH3:6])[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:13][C@@H:14]4[CH2:20]3)=[N:23][CH:24]=2)[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86680532HCID 86680532, compound

Product 1

HCID 86680531HCID 86680531, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product from Example 193A (11 mg, 0.022 mmol) in a mixture of 1,4-dioxane (0.5 mL) and hydrogen chloride solution (4 N in 1,4-dioxane) (0.5 mL, 2.00 mmol) was stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound (4.3 mg, 49%). 1H NMR (300 MHz, CDCl3) δ ppm 0.83-1.02 (m, 4 H) 1.19-3.25 (m, 13 H) 3.49-3.97 (m, 2 H) 4.42 (d, J=17.90 Hz, 1 H) 4.58-4.90 (m, 1 H) 5.20-5.42 (m, 1 H) 7.20-7.42 (m, 5 H) 7.86-8.07 (m, 2 H); MS (ESI) m/z 408 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between saturated aqueous NaHCO3 solution and dichloromethane
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2bfadb9135741068c15cfc4cf625105
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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