Beta-Propiolactone → HCID 54182937, compound

HRID 1107147Notes

Reaction equation

HRID 1107147 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].[CH3:14][C@H:15]1[C@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:17][C:16]1=[O:29].O1CCC1=O.Cl.CCOCC>C(O)(C)C.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@H:15]([CH3:14])[C:16]([OH:29])=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

8

Reactant 5

HCID 2365Beta-PropiolactoneHCID 14798Sodium HydroxideHCID 1365393,4-Dimethoxybenzene-1-thiolHCID 10680344HCID 10680344, compoundHCID 10953452Ether hydrochloride

Product 1

HCID 54182937HCID 54182937, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3,4-dimethoxybenzenethiol (0.33 g, 1.9 mmol) in isopropanol (3 mL) is cooled in an ice-bath and 1 M sodium hydroxide (1.4 mL, 1.4 mmol) is added over 2 minutes. (3S,4S)-3-Methyl-4-(4-phenylbutyl)oxetan-2-one (0.28 g, 1.3 mmol) is dissolved in isopropanol (3 mL) and cooled to 0° C. Then the thiolate is added to the oxetanone solution over 3 minutes. This mixture is stirred with ice cooling for 5 minutes and then allowed to come to room temperature and stir 3 hours. The reaction is then acidified to pH 5 with HCl/ether. Methanol is added and the reaction mixture azeotroped several times until a semi-solid residue is obtained. The crude product is purified by column chromatography (silica, 1% MeOH in CH2Cl2) to give (2R,3R)-3-(3,4-dimethoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid (0.35 g, 69%): 1H NMR (300 MHz, CDCl3) δ 7.28-7.23 (m, 2H), 7.19-7.11 (m, 3H), 7.04-6.97 (m, 2H), 6.76 (d, J=8.3 Hz, 1H), 3.84 (s, 3H), 3.83 (s, 3H), 3.27-3.25 (m, 1H), 2.72-2.68 (m, 1H), 2.56 (t, J=7.1 Hz, 2H), 1.63-1.47 (m, 6H), 1.26 (d, J=7.1 Hz, 3H); MS (EI) m/e 389 (M+H)+.

Workup

  1. customto come to room temperature
  2. stirringstir 3 hours
  3. customthe reaction mixture azeotroped several times until a semi-solid residue
  4. customis obtained
  5. customThe crude product is purified by column chromatography (silica, 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-baab9a6e01324d5aa2db20cb871341e6
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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