Hydrochloric Acid → HCID 58593383, compound

HRID 916994Notes

Reaction equation

HRID 916994 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([S:11][C:12]([S:15][C:16]2[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([O:26][CH2:27][CH2:28][CH2:29][C@@H:30]3[CH2:34][O:33]C(C)(C)[O:31]3)=[C:18]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:17]=2)([CH3:14])[CH3:13])[CH:8]=[C:7]([C:41]([CH3:44])([CH3:43])[CH3:42])[C:6]=1[OH:45])([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[K+]>CO>[C:22]([C:20]1[CH:21]=[C:16]([S:15][C:12]([S:11][C:9]2[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:45])=[C:7]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:8]=2)([CH3:14])[CH3:13])[CH:17]=[C:18]([C:37]([CH3:40])([CH3:39])[CH3:38])[C:19]=1[O:26][CH2:27][CH2:28][CH2:29][C@H:30]([OH:31])[CH2:34][OH:33])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86602765HCID 86602765, compound

Product 1

HCID 58593383HCID 58593383, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2,6-di-tert-butyl-4-(1-{3,5-di-tert-butyl-4-[3-(2,2-dimethyl-[1,3]dioxo-lan-4(R)-yl)-propoxy]-phenylsulfanyl}-1-methyl-ethylsulfanyl)-phenol (Ex-11, 230 mg, 0.35 mmol) in 20 ml MeOH, was added 1.0 N HCl dropwise until the mixture turned cloudy. Then small amount of MeOH was added to the mixture until it became clear. The mixture was stirred at room temperature, and HPLC indicated that the reaction completed within 2 hours. The mixture was neutralized with 5N KOH and extracted with EtOAc. The combined organic phase was washed with water, dried over MgSO4, and concentrated to dryness. The residue was purified by silica gel column chromatography to give 0.2 g (93%) 5-{2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenoxy}-pentane-1,2(S)-diol as a white solid, mp 68–71° C. 1H-NMR (CDCl3) δ 7.53 (s, 2H), 7.45 (s, 2H), 5.36(s, 1H), 3.67–3.79 (m, 4H), 3.46–3.52 (m, 1H), 1.91–2.17 (m, 4H), 1.42–1.45 (m, 42H). MS m/z: 636.4119 ([M+NH4]+, 20%). Anal. calcd for C36H58O4S2: C, 69.86; H, 9.44; S, 10.36; found: C, 70.10; H, 9.15, S, 10.13.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-24b73eed2dfb45738b37a0c49932c614
Source dataset
uspto-grants-2007_09
Patent number
US07271274B2

Reaction notes

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