1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,4-bis(nitrooxy)butyl (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoate

HRID 1437608Notes

Reaction equation

HRID 1437608 reaction equation
[C:1]([O:4][CH2:5]/[C:6](/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[C:7](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[N+:27]([O:30][CH:31]([CH2:35][O:36][N+:37]([O-:39])=[O:38])[CH2:32][CH2:33]O)([O-:29])=[O:28].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:4][CH2:5]/[C:6](/[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[C:7](/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)\[C:8]([O:10][CH2:33][CH2:32][CH:31]([O:30][N+:27]([O-:29])=[O:28])[CH2:35][O:36][N+:37]([O-:39])=[O:38])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11617716(Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acidHCID 579416243,4-Bis(nitrooxy)butyl alcohol

Product 1

HCID 113074053,4-bis(nitrooxy)butyl (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoateYield 44%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.72 g of (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 30 mL of CH2Cl2 at 0° C. was added 750 mg of 3,4-bis(nitrooxy)butyl alcohol, 560 mg of DMAP and 880 mg of EDCI. The mixture was stirred at RT for 2 h then quenched by addition of NH4Cl sat., extracted with EtOAc, washed with NaHCO3 sat., brine and dried over sodium sulfate. Purification by flash chromatography afforded 930 mg of the titled compound as a white solid. 1H NMR (acetone-d6, 500 MHz): δ 7.77 (d, 2H), 7.43 (d, 2H), 7.17-7.15 (m, 3H), 7.08 (dd, 2H), 5.56-5.52 (m, 1H), 5.22 (s, 2H), 4.95 (dd, 1H), 4.69 (dd, 1H), 4.47-4.41 (m, 2H), 3.05 (s, 3H), 2.32-2.19 (m, 2H), 1.89 (s, 3H).

Workup

  1. customthen quenched by addition of NH4Cl sat.
  2. extractionextracted with EtOAc
  3. washwashed with NaHCO3 sat., brine
  4. dry with materialdried over sodium sulfate
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-1f24a06b107741e28ab32f6d0c0323ae
Source dataset
uspto-grants-2009_11
Patent number
US07622502B2

Reaction notes

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