Sodium triacetoxyborohydride → HCID 58504098, compound

HRID 2407686Notes

Reaction equation

HRID 2407686 reaction equation
Cl.[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]([CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:8]2=[O:14].[C:22]1([C:28]2[CH:32]=[C:31]([CH:33]=O)[O:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(N(C(C)C)CC)(C)C>[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]([CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:33][C:31]3[O:30][N:29]=[C:28]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:32]=3)[CH2:18][CH2:17]1)[C:8]2=[O:14]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 113672673-Phenyl-1,2-oxazole-5-carbaldehydeHCID 66989815HCID 66989815, compound

Product 1

HCID 58504098HCID 58504098, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

The compound prepared in Example 77 (0.041 g), the compound prepared in Example 7 (0.026 g) and sodium triacetoxyborohydride (0.074 g) were suspended in dichloromethane (5 mL) and diisopropylethylamine (0.10 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=3:1) to obtain the title compound (0.029 g) having the following physical data.

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-de5ce5c3cf88406ebd4267de4467984a
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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