Acetone → HCID 57551751, compound

HRID 907313Notes

Reaction equation

HRID 907313 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([CH:28]=[C:29]([F:32])[C:30]=4[CH3:31])[C:22]([NH:24][CH:25]4[CH2:27][CH2:26]4)=[O:23])[CH:17]=3)[C:12](=[O:33])[N:11]([CH2:34][CH:35]3[CH2:37][CH2:36]3)[CH:10]=2)[CH2:4][CH2:3]1.[CH3:38][C:39]([CH3:41])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:25]1([NH:24][C:22](=[O:23])[C:21]2[CH:28]=[C:29]([F:32])[C:30]([CH3:31])=[C:19]([C:16]3[CH:17]=[C:18]4[C:13](=[CH:14][CH:15]=3)[C:12](=[O:33])[N:11]([CH2:34][CH:35]3[CH2:36][CH2:37]3)[CH:10]=[C:9]4[CH2:8][N:5]3[CH2:6][CH2:7][CH:2]([NH:1][CH:39]([CH3:41])[CH3:38])[CH2:3][CH2:4]3)[CH:20]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 57551836HCID 57551836, compound

Product 1

HCID 57551751HCID 57551751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 83 (50 mg) was dissolved in dichloromethane (10 mL) and acetone (0.037 mL) added. The solution was stirred for 5 minutes then sodium triacetoxyborohydride (63.3 mg) added. The mixture was stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure and the residue purified by HPLC to give the title compound as a solid (45 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-f2213de08cd2441182793de2db78f7ce
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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