1-Butanol → HCID 135816376, compound

HRID 990242Notes

Reaction equation

HRID 990242 reaction equation
C[Si]([N-:5][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:13][C:14]1[C:19]([C:20]2[NH:21][C:22](=[O:38])[C:23]3[C:24](=[C:26]([CH2:36][CH3:37])[N:27]([CH2:29][C:30]4[N:31]=[N:32][CH:33]=[CH:34][CH:35]=4)[N:28]=3)[N:25]=2)=[CH:18][C:17]([S:39]([N:42]2[CH2:47][CH2:46][N:45]([CH2:48][CH3:49])[CH2:44][CH2:43]2)(=[O:41])=[O:40])=[CH:16][N:15]=1)[CH3:12].[CH2:50](O)[CH2:51]CC>>[NH3:5].[CH2:11]([O:13][C:14]1[C:19]([C:20]2[NH:21][C:22](=[O:38])[C:23]3[C:24](=[C:26]([CH2:36][CH3:37])[N:27]([CH2:29][C:30]4[N:31]=[N:32][CH:33]=[CH:34][CH:35]=4)[N:28]=3)[N:25]=2)=[CH:18][C:17]([S:39]([N:42]2[CH2:47][CH2:46][N:45]([CH2:48][CH3:49])[CH2:44][CH2:43]2)(=[O:41])=[O:40])=[CH:16][N:15]=1)[CH2:12][CH2:50][CH3:51]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 135816345HCID 135816345, compound

Product 2

HCID 222AmmoniaHCID 135816376HCID 135816376, compoundYield 59%

Conditions

Temperature
110 °C

Procedure

Potassium bis(trimethylsilyl)amide (35 mg, 0.176 mmol) was added to a solution of the title compound of Example 146 (80 mg, 0.145 mmol) in n-butanol (2 ml), and the reaction stirred at 110° C. for 6½ hours. The cooled mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate (20 ml) and sodium bicarbonate solution (10 ml). The phases were separated, the organic layer washed with additional sodium bicarbonate solution (10 ml), brine (10 ml), dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (100:0:0 to 99.6:0.4:0.5) to afford the title compound (50 mg, 59%) as a white foam.

Workup

  1. concentrationThe cooled mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate (20 ml) and sodium bicarbonate solution (10 ml)
  3. customThe phases were separated
  4. washthe organic layer washed with additional sodium bicarbonate solution (10 ml), brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-261b172dc13f4a8989b7838d29a160e9
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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