HCID 21059932, compound → HCID 86595785, compound

HRID 1241446Notes

Reaction equation

HRID 1241446 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[S:25])[NH2:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.O.O.[OH-].C(=O)(O)[O-].[Mg+2].[O:37]1[C:41]2[CH:42]=[CH:43][C:44]([C@@H:46]([CH2:53][C:54](=O)[CH2:55]Cl)[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:45][C:40]=2[O:39][CH2:38]1>O1CCOCC1>[O:37]1[C:41]2[CH:42]=[CH:43][C:44]([C@@H:46]([CH2:53][C:54]3[N:24]=[C:23]([CH2:22][CH2:21][CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[S:25][CH:55]=3)[CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:45][C:40]=2[O:39][CH2:38]1

Participants

5

Reactant 3

HCID 21059932HCID 21059932, compoundHCID 5324963056378-72-4HCID 86595786HCID 86595786, compound

Product 1

HCID 86595785HCID 86595785, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 5-{[tert-butyl(diphenyl)silyl]oxy}pentanethioamide (4.97 g, 13.37 mmol) in 1,4-dioxane (50 mL). Add magnesium carbonate hydroxide pentahydrate (3.25 g, 0.5 mmol) and (3S)-ethyl 3-(1,3-benzodioxol-5-yl)-6-chloro-5-oxohexanoate (see Scheme 2, Example M) (4.18 g, 13.37 mmol). Heat to 60° C. for 5 hrs. Upon cooling, the reaction was filtered through a pad of celite and concentrated in vacuo, and purified via silica gel chromatography (eluent: 9:1 Hexane:Ethyl Acetate) to give the product as a yellow oil. Yield: 6.55 g (78%) 1H NMR (DMSO-d6) δ7.64–7.58 (m, 4H), 7.48–7.39 (m, 6H), 6.95–6.93 (m, 1H), 6.85–6.82 (m, 1H), 6.73–6.69 (m, 1H), 5.92 (s, 2H), 3.93–3.85 (q, 2H), 3.70–3.64 (t, 2H), 3.46–3.38 (m, 1H), 3.00–2.85 (m, 4H), 2.68–2.53 (m, 2H), 1.83–1.74 (m, 2H), 1.62–1.53 (m, 2H), 1.08–0.99 (t, 3H), 0.99 (s, 9H).

Workup

  1. temperatureUpon cooling
  2. filtrationthe reaction was filtered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. custompurified via silica gel chromatography (eluent: 9:1 Hexane:Ethyl Acetate)

Sources & evidence

ORD record
ord-ec8f1999128042ab96cea308163aab15
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

Loading…