Acetic Acid → HCID 57223582, compound

HRID 1107179Notes

Reaction equation

HRID 1107179 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.COC1C=C[C:15]([S:18]([C@@H:21]([C@@H:32]2[CH2:35][O:34][C:33]2=[O:36])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(O)(=O)C.[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>>[CH3:43][O:44][C:45]1[CH:41]=[CH:42][C:15]([S:18]([C@@H:21]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:32]([CH2:35][S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:33]([OH:36])=[O:34])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 7969ThiophenolHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 53923612HCID 53923612, compound

Product 1

HCID 57223582HCID 57223582, compoundYield 82%

Procedure

A 60% suspension of NaH in mineral oil (84 mg, 2.2 mmol) is carefully added to a solution of thiophenol (0.30 g, 2.7 mmol) in THF (10 mL) at 0° C. The mixture is allowed to warm to ambient temperature and is transferred to a solution of (±)-3-(R*)-[1-(R*)-(4-methoxybenzenesulfonyl)-5-phenylpentyl]-oxetan-2-one (0.63 g, 1.6 mmol) in THF (10 mL). The reaction is stirred 14 hours and then acidified with acetic acid. The crude mixture is azeotroped with methanol (2×50 mL) and purified by column chromatography using gradient elution (silica, 1 to 3% MeOH in CH2Cl2) to yield pure (±)-(2R*,3S*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(phenylsulfanylmethyl)heptanoic acid (0.64 g, 82%): m.p. 133-135; 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J=8.6 Hz, 2H), 7.30-7.17 (m, 8H), 7.06 (d, J=7.3 Hz, 2H), 6.93 (d, J=8.6 Hz, 2H), 3.84 (s, 3H), 3.63 (bs, 1H), 3.52 (dd, J=14.2, 7.7 Hz, 1H), 3.14 (dd, J=14.2, 5.2 Hz, 1H), 2.98 (bs, 1H), 2.43 (t, J=7.4 Hz, 2H), 1.95-1.83 (m, 1H), 1.78-1.62 (m, 1H), 1.50-1.34 (m, 2H), 1.28-1.07 (m, 2H); MS (FAB) m/e 489 (M+); Anal. (C27H30O5S2) C, H, N.

Workup

  1. customThe crude mixture is azeotroped with methanol (2×50 mL)
  2. custompurified by column chromatography
  3. washelution (silica, 1 to 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6ff286986235427dabf846013424a413
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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