Acetic Acid → HCID 22254180, compound

HRID 1611717Notes

Reaction equation

HRID 1611717 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14](=[C:15]=O)[CH:13]=[CH:12][C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:10]1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C(O)(=O)C.O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=[CH:13][C:14]=1[CH2:15][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8083MorpholineHCID 131725264HCID 131725264, compound

Product 1

HCID 22254180HCID 22254180, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

(1M in THF) is added to a solution of aldehyde 8 (50 mg, 0.121 mmol), morpholine (2eq) and glacial acetic acid (5 ml) dissolved in THF (5 ml) at room temperature with stirring. The mixture is heated to 70° C. for 18 h, after which, a slow addition of water (1 ml) is used to decompose excess reagent. The mixture is partitioned between ethyl acetate (30 ml) and saturated citric acid solution (10 ml). The organic layer is discarded, and the aqueous layer is carefully basified with 1M aq. sodium hydroxide to pH 9. Then the basic aqueous layer is extracted with ethyl acetate (2×25 ml). The combined organic layers are dried (sodium sulfate), concentrated, and purified by chromatography (silica gel, 10% methanol/methylene chloride) to afford pure product 9 (52% yield).

Workup

  1. customThe mixture is partitioned between ethyl acetate (30 ml) and saturated citric acid solution (10 ml)
  2. extractionThen the basic aqueous layer is extracted with ethyl acetate (2×25 ml)
  3. dry with materialThe combined organic layers are dried (sodium sulfate)
  4. concentrationconcentrated
  5. custompurified by chromatography (silica gel, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-bee9b401346e4079b40c555fa23570ca
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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