Acetic Acid → HCID 68180898, compound

HRID 2167108Notes

Reaction equation

HRID 2167108 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([N:11]([CH:20]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][NH:15]3)[CH:9]=[CH:10][C:2]1=2.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:33](C)=O.[Na+].CC(O)=O>ClCCCl.C(OCC)(=O)C.[OH-].[Na+]>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([N:11]([CH:20]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][N:15]3[CH3:33])[CH:9]=[CH:10][C:2]1=2

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68180984HCID 68180984, compound

Product 1

HCID 68180898HCID 68180898, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of compound 60 (0.5 g, 1.32 mmol) in DCE (25 mL) were added formaldehyde (35% solution in H2O, 0.17 mL, 1.98 mmol), Na(OAc)3BH (0.84 g, 3.96 mmol) and AcOH (0.2 mL) successively at 0° C. and the mixture was stirred at rt for 16 hours. The reaction mixture was dissolved in ethyl acetate and basified with 1N NaOH. The organic layer was separated and washed with water and brine. The solution was dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by Combiflash® chromatography eluting with 5-5.2% methanol-DCM to provide compound 61.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialThe solution was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by Combiflash® chromatography
  7. washeluting with 5-5.2% methanol-DCM

Sources & evidence

ORD record
ord-5bcd80f4b0cd41f192c7ead49387fb1c
Source dataset
uspto-grants-2015_06
Patent number
US09044482B2

Reaction notes

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