Acetic Acid → HCID 68751446, compound

HRID 1864801Notes

Reaction equation

HRID 1864801 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:22][CH2:23][C:24]2[O:28][CH:27]=[C:26]([C:29]3[CH:57]=[CH:56][C:32]4[N:33]([C:37]([C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:34](=[O:36])[O:35][C:31]=4[CH:30]=3)[CH:25]=2)[CH2:18][CH2:17]1.[F:58][C:59]1[CH:66]=[CH:65][C:62]([CH:63]=O)=[CH:61][CH:60]=1.C(O)(=O)C>ClCCCl.C(Cl)(Cl)Cl>[F:58][C:59]1[CH:66]=[CH:65][C:62]([CH2:63][N:22]([CH2:23][C:24]2[O:28][CH:27]=[C:26]([C:29]3[CH:57]=[CH:56][C:32]4[N:33]([C:37]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)[C:50]5[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=5)[C:34](=[O:36])[O:35][C:31]=4[CH:30]=3)[CH:25]=2)[CH:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)=[CH:61][CH:60]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68751986HCID 68751986, compound

Product 1

HCID 68751446HCID 68751446, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

Sodium triacetoxyborohydride (71 mg, 0.33 mmol) was added to a solution of 6-{5-[(1-methyl-piperidin-4-ylamino)-methyl]-furan-3-yl}-3-trityl-3H-benzooxazol-2-one (95 mg, 0.17 mmol) and 4-fluorobenzaldehyde (21 mg, 0.2 mmol) and acetic acid (20 mg, 0.33 mmol) in 1.5 mL of 1,2-dichloroethane. The mixture was stirred at ambient temperature for 20 h, and then it was diluted with chloroform and washed with saturated sodium carbonate solution. The aqueous phase was extracted with chloroform, and the combined organic phases were washed with water and brine, dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with dichloromethane/methanol) gave 64 mg of product.

Workup

  1. washwashed with saturated sodium carbonate solution
  2. extractionThe aqueous phase was extracted with chloroform
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto leave the crude product
  8. washChromatography (elution with dichloromethane/methanol)

Sources & evidence

ORD record
ord-e6d8ab56ad7844d68ce9aeb10f05ac91
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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