Hydrochloric Acid → HCID 68610704, compound

HRID 1991140Notes

Reaction equation

HRID 1991140 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:20]([C:21]5[CH2:22][N:23]([CH3:26])[NH:24][CH:25]=5)=[CH:19][N:18]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:15]4=[N:16][CH:17]=3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.O>C1COCC1>[CH3:26][N:23]1[CH2:22][C:21]([C:20]2[C:14]3[C:15](=[N:16][CH:17]=[C:12]([CH2:11][CH:8]4[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]4)[CH:13]=3)[N:18]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[CH:19]=2)=[CH:25][NH:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68608088HCID 68608088, compound

Product 1

HCID 68610704HCID 68610704, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 87 (307 mg, 0.64 mmol) in THF (20 mL) was added 6.0 N aq. HCl solution (7 mL) and the reaction mixture was allowed to stir at r.t. for 1 h. Water (50 mL) was then added, and the mixture extracted with AcOEt (2×75 mL). The combined organic solutions were dried (MgSO4) and concentrated to afford 88 as a clear oil (261 mg, 0.59 mmol, 93%). 1H NMR (400 MHz, CDCl3) δ 0.00 (s, 9H), 0.99 (t, J=8.2 Hz, 2H), 1.49-1.62 (m, 2H), 2.07-2.16 (m, 2H), 2.31-2.49 (m, 5H), 2.82 (d, J=6.7 Hz, 2H), 3.65 (t, J=8.3 Hz, 2H), 4.07 (s, 3H), 5.77 (s, 2H), 7.49 (s, 1H), 7.69 (s, 1H), 7.83 (s, 1H), 7.92 (s, 1H), 8.27 (s, 1H).

Workup

  1. extractionthe mixture extracted with AcOEt (2×75 mL)
  2. dry with materialThe combined organic solutions were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0c7df8f183a04ada95666bf31b6ad09e
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

Loading…