Methanol → 4-[3-[6-(3-Bromo-5-methanesulfonyloxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

HRID 416979Notes

Reaction equation

HRID 416979 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[C:24]([Br:30])[CH:23]=2)[C:10]=1[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH3:2].[CH3:39][S:40](Cl)(=[O:42])=[O:41].CO.CCOC(C)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4](=[O:38])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([CH2:28][O:29][S:40]([CH3:39])(=[O:42])=[O:41])[CH:25]=[C:24]([Br:30])[CH:23]=2)[C:10]=1[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 594968024-[3-[6-(3-Bromo-5-hydroxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 594968294-[3-[6-(3-Bromo-5-methanesulfonyloxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-[6-(3-Bromo-5-hydroxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.99 g, 5.05 mmol) in DCM (100 mL), TEA (3.52 mL, 25.26 mmol), DMAP (62 mg, 0.505 mmol) were added, followed by MsCl (0.60 mL, 7.58 mmol), and stirred at room temperature for 2.5 h. MeOH (4 mL) was added to quench the reaction. The solvent was removed under reduced pressure. Flash column chromatography (40% EtOAc/Hex) provided a colorless oil (2.51 g, 74% yield). 1H NMR (CDCl3): δ 7.11-7.05 (m, 3H), 6.86 (s, 1H), 6.77 (d, 1H), 6.68 (d, 1H), 5.14 (s, 2H), 4.17-4.08 (m, 4H), 4.01-3.91 (m, 4H), 2.99-2.93 (m, 5H), 2.63 (dd, 2H), 2.56-2.46 (m, 4H), 2.17-0.89 (m, 16H).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8a90f41a0a1943d2913a510ce7c345f8
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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