Acetic Acid → HCID 60026333, compound

HRID 400680Notes

Reaction equation

HRID 400680 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:32])([CH3:31])[CH2:12][C:13]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH2:14][C:15]2[NH:23][C:22]3[C:17](=[N:18][C:19]([CH:24]=O)=[CH:20][CH:21]=3)[CH:16]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.C(O)(=O)C.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>ClC(Cl)C.C(OCC)(=O)C.[OH-].[NH4+]>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:32])([CH3:31])[CH2:12][C:13]([CH2:14][C:15]2[NH:23][C:22]3[C:17](=[N:18][C:19]([CH2:24][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[CH:20][CH:21]=3)[CH:16]=2)([OH:30])[C:26]([F:29])([F:27])[F:28])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 8083MorpholineHCID 60026669HCID 60026669, compound

Product 1

HCID 60026333HCID 60026333, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of the aldehyde of Example 94 (0.050 g, 0.107 mmol) and 0.078 mL of acetic acid in 3.0 mL of dichloroethane was added morpholine (0.233 mL, 2.68 mmol) at 0° C. The reaction was allowed to stir at room temperature for 30 minutes. To this yellow solution was added triacetoxy sodium borohydride (0.057 mg, 0.268 mmol), then continued stirring at room temperature for 14 hours. The reaction mixture was diluted with 10 mL of ethyl acetate and 2 mL of 3% ammonium hydroxide solution. The biphasic system was separated and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with three 20 mL portions of water, brine, dried over sodium sulfate, filtered and the solvent was evaporated in vacuo to give yellow oil. This crude material was applied onto a flash column and eluted with 5% MeOH—CH2Cl2, 0.5% NH4OH, to give the title compound (0.018 g, 32.0% yield) as a white foam.

Workup

  1. stirringcontinued stirring at room temperature for 14 hours
  2. customThe biphasic system was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic layers were washed with three 20 mL portions of water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated in vacuo
  8. customto give yellow oil
  9. washeluted with 5% MeOH—CH2Cl2, 0.5% NH4OH

Sources & evidence

ORD record
ord-035ffce9616a4ff2b0705f59c59c81ea
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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