Acetic Acid → HCID 68181210, compound

HRID 2167103Notes

Reaction equation

HRID 2167103 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:28](C)=O.[Na+].C(O)(=O)C>ClCCCl.C(OCC)(=O)C.[OH-].[Na+]>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]1[CH3:28]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68181019HCID 68181019, compound

Product 1

HCID 68181210HCID 68181210, compound

Reagents, catalysts & solvents 3

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

Procedure

To a stirred solution of compound 53 (0.53 g, 1.62 mmol) in DCE (25 mL) were added successively formaldehyde (35% solution in H2O, 0.2 mL, 2.43 mmol), Na(OAc)3BH (1.03 g, 4.86 mmol) and acetic acid (0.2 mL) at 0° C., and the solution was allowed to stir at rt for 16 hours. The reaction mixture was diluted with ethyl acetate and basified with 1N NaOH solution. The organic layer was separated and washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by chromatography on neutral alumina eluting 1% methanol-DCM to get compound 54.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography on neutral alumina eluting 1% methanol-DCM

Sources & evidence

ORD record
ord-5e9c519fb2a94751845ee75d45192516
Source dataset
uspto-grants-2015_06
Patent number
US09044482B2

Reaction notes

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