Dimethylformamide dimethyl acetal → HCID 66671931, compound

HRID 239013Notes

Reaction equation

HRID 239013 reaction equation
[C:1]([C:4]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][C:7]([O:8][CH2:9][C:10]2([NH:13][C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:12][CH2:11]2)=[C:6]([O:29][CH3:30])[CH:5]=1)(=[O:3])[CH3:2].CO[CH:33](OC)[N:34]([CH3:36])[CH3:35]>CN(C=O)C.O>[CH3:33][N:34]([CH3:36])[CH:35]=[CH:2][C:1]([C:4]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][C:7]([O:8][CH2:9][C:10]2([NH:13][C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:12][CH2:11]2)=[C:6]([O:29][CH3:30])[CH:5]=1)=[O:3]

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 46913784HCID 46913784, compound

Product 1

HCID 66671931HCID 66671931, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the compound of Example 2 (1.7 g, 4.1 mmol) and N,N-dimethylformamide dimethylacetal (0.9 g, 8.2 mmol) in DMF (6 mL) was stirred at 100° C. for 2 h. After cooling at room temperature, the reaction mixture was diluted with water (30 mL) and extracted with AcOEt (3×50 mL). The combined organic phases were washed with brine (2×50 mL), dried and evaporated to give 1-[(4-(3-dimethylaminopropenoyl)-2-methoxy-5-nitrophenoxy)methyl]-N-benzyloxycarbonyl-1-aminocyclopropane (1.9 g, yield: 95%) as a yellow solid.

Workup

  1. temperatureAfter cooling at room temperature
  2. extractionextracted with AcOEt (3×50 mL)
  3. washThe combined organic phases were washed with brine (2×50 mL)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-89f509001bcc43758e2ef1f6e2619bf4
Source dataset
uspto-grants-2014_02
Patent number
US08642767B2

Reaction notes

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