Hydrochloric Acid → HCID 21829818, compound

HRID 1600521Notes

Reaction equation

HRID 1600521 reaction equation
[CH2:1]([O:3][CH:4]([O:9][CH2:10][CH3:11])[CH2:5][CH2:6][CH2:7][NH2:8])[CH3:2].COC(N1[C:20](=[O:21])[CH:19]=[CH:18][C:17]1=[O:22])=O.O1CCCC1.Cl>C(=O)(O)[O-]>[CH2:10]([O:9][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][CH2:7][N:8]1[C:20](=[O:21])[CH:19]=[CH:18][C:17]1=[O:22])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 806724,4-DiethoxybutylamineHCID 580610N-(Methoxycarbonyl)maleimide

Product 1

HCID 21829818HCID 21829818, compound

Reagents, catalysts & solvents 1

HCID 769Bicarbonate IonSolvent

Procedure

As shown in FIG. 2, to a solution of 4-aminobutyraldehyde diethylacetal (5 g, 31 mmol) in 100 ml of saturated bicarbonate was added N-methoxycarbonylmaleimide (4.91 g, 31.6 mmol) at 0° C. (icebath). After 15 minutes, tetrahydrofuran (100 ml) was added at room temperature and the resultant mixture stirred for 1 hour. The resultant mixture was then acidified with 1 N hydrochloric acid to pH 6-7 and extracted with ethyl acetate (3×200 ml). The combined organic extracts were dried (MgSO4) and evaporated in vacuo. The crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate/petroleum ether 1:2 to yield 4-maleimidobutyraldehyde diethylacetal as a yellow oil (4.31 g; 58%), TLC Rf=0.65, ethyl acetate/hexane 1:1.

Workup

  1. extractionextracted with ethyl acetate (3×200 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customevaporated in vacuo
  4. customThe crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate/petroleum ether 1:2

Sources & evidence

ORD record
ord-fd30633cacac48598e717afaece4eb6e
Source dataset
uspto-grants-1999_11
Patent number
US05976857

Reaction notes

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