Water → HCID 178471770, compound

HRID 220147Notes

Reaction equation

HRID 220147 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:24](OC)[N:25]([CH3:27])[CH3:26].O>CN(C)C=O>[CH3:24][N:25]([CH3:27])/[CH:26]=[CH:2]/[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 178471767HCID 178471767, compound

Product 1

HCID 178471770HCID 178471770, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 26A (2.14 g, 7.42 mmol) and N,N-dimethylformamide dimethylacetal (1.42 g, 11.9 mmol) in N,N-dimethylformamide (20 mL) were heated at 100° C. for 16 h. The solution was cooled to room temperature, and water (20 mL) was added over a period of 10 min. The precipitate was collected by filtration, washed with water (3×20 mL), and dried in vacuo at 50° C. for 24 h to give crude product. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.11-1.21 (m, 5H), 1.43-1.55 (m, 2H), 1.63-1.82 (m, 5H), 2.22 (d, J=6.76 Hz, 2H), 2.43-2.47 (m, 1H), 2.90 (s, 3H), 3.12 (s, 3H), 4.07 (q, J=7.06 Hz, 2H), 5.79 (d, J=12.27 Hz, 1H), 7.27 (d, J=8.59 Hz, 2H), 7.67 (d, J=12.27 Hz, 1H), 7.79 (d, J=8.59 Hz, 2H); MS (ESI) m/z 344.1.0 [M+H]+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water (3×20 mL)
  3. customdried in vacuo at 50° C. for 24 h
  4. customto give crude product

Sources & evidence

ORD record
ord-c81b71b154d84f9da6132f7355cb93ef
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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