1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5,6-bis(nitrooxy)hexyl (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoate

HRID 1437601Notes

Reaction equation

HRID 1437601 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]([CH2:37][O:38][N+:39]([O-:41])=[O:40])[CH2:32][CH2:33][CH2:34][CH2:35]O)([O-:29])=[O:28].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CC(O)=O>[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][CH2:35][CH2:34][CH2:33][CH2:32][CH:31]([O:30][N+:27]([O-:29])=[O:28])[CH2:37][O:38][N+:39]([O-:41])=[O:40])=[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 579416215,6-Bis(nitrooxy)hexan-1-ol

Product 1

HCID 113306865,6-bis(nitrooxy)hexyl (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoateYield 63.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2.5 g of (2Z)-4-(acetyloxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid, 10 mmol of 5,6-bis(nitrooxy)hexan-1-ol, 15 mmol of DMAP and 10 mmol of EDCI was stirred at rt for 3 h. Then, AcOH (2-mL) was added and the mixture was filtered through a pad of silica gel and washed with EtOAc, evaporated, purified by flash chromatography (15-50% EtOAc/hexane) to afford 2.45 g of the desired compound as a white solid. 1H NMR (acetone-d6, 500 MHz): δ 7.79 (d, 2H), 7.45 (d, 2H), 7.21-7.16 (m, 1H), 7.13-7.08 (m, 2H), 5.52-5.44 (m, 1H), 5.21 (s, 1H), 4.98 (dd, 1H), 4.72 (dd, 1H), 4.29 (t, 2H), 3.09 (s, 3H), 1.92 (s, 3H), 1.89-1.74 (m, 4H), 1.60-1.48 (m 2H).

Workup

  1. filtrationthe mixture was filtered through a pad of silica gel
  2. washwashed with EtOAc
  3. customevaporated
  4. custompurified by flash chromatography (15-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-e7061a67e2044e43a2933f475992b4f4
Source dataset
uspto-grants-2009_11
Patent number
US07622502B2

Reaction notes

Loading…