Sodium Hydroxide → HCID 90411028, compound

HRID 1754610Notes

Reaction equation

HRID 1754610 reaction equation
C([Si](C)(C)[O:6][CH2:7][C@H:8]([CH2:19][N:20]1[CH:25]=[C:24]([CH3:26])[C:23](=[O:27])[N:22](C(=O)C2C=CC=CC=2)[C:21]1=[O:36])[C@H:9]([O:11][Si](C(C)(C)C)(C)C)[CH3:10])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[OH-].[Na+]>C1COCC1.CO.O>[CH3:26][C:24]1[C:23](=[O:27])[NH:22][C:21](=[O:36])[N:20]([CH2:19][C@H:8]([C@H:9]([OH:11])[CH3:10])[CH2:7][OH:6])[CH:25]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 90411488HCID 90411488, compound

Product 1

HCID 90411028HCID 90411028, compoundYield 77.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 32 (1.9 g, 3.38 mmol) in 20 ml of THF was added 6 ml of 1 M TBAF in THF. After being kept at room temperature for 2 hrs the reaction was diluted with methanol (100 ml), water (100 ml) and treated with 10 ml of 1 M NaOH. The reaction was allowed to proceed overnight, then combined with 10 g of Dowex 66 and 20 g of Dowex 50 w×8×200 and stirred for 1 h. The resin was removed by filtration, washed with 50% methanol and the combined filtrates concentated to afford 0.6 g (77%) of 33 as a white solid. This material contained some impurities but was considered to be pure enough for further use without additional purification.

Workup

  1. waitto proceed overnight
  2. customThe resin was removed by filtration
  3. washwashed with 50% methanol

Sources & evidence

ORD record
ord-0f75121a200a42b697ac601c4e3befd2
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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