Benzaldehyde → HCID 67059776, compound

HRID 1671288Notes

Reaction equation

HRID 1671288 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:7][N:8]2[C:11]2[S:12][CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=2)=[CH:4][CH:3]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl.C(O)(=O)C>[CH2:27]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[N:7][N:8]2[C:11]2[S:12][CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=2)=[CH:4][CH:3]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 67059738HCID 67059738, compound

Product 1

HCID 67059776HCID 67059776, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 4 (10 mg) in dichloromethane (350 μL, manufactured by Kanto Chemical Co., Inc.), acetic acid (10 μL, manufactured by Wako Pure Chemical Industries, Ltd.), benzaldehyde (4 mg, manufactured by Nacalai Tesque, Inc.) and sodium triacetoxyborohydride (17.7 mg, manufactured by Sigma-Aldrich Corp.) were added, and the mixture was stirred overnight at room temperature. Water (1 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (3×2 mL), washed with brine (10 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1), to give 2.4 mg of the title compound. LC-MS: HPLC retention time 5.83 minutes, m/z 519 (M+H), condition B-1.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×2 mL)
  2. washwashed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was then evaporated
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-f92ca3efcc104d6693600249a0c21276
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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