m-Chloroperbenzoic acid → HCID 11699779, compound

HRID 32851Notes

Reaction equation

HRID 32851 reaction equation
[CH2:1]([S:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:38])[C@@H:11]([N:20]2[C:24](=[O:25])[C@@H:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][CH3:36])=[CH:28][CH:27]=3)[NH:22][C:21]2=[O:37])[C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[S:7][CH:8]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:47])C=1>O1CCCC1>[CH2:1]([S:3]([C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:38])[C@@H:11]([N:20]2[C:24](=[O:25])[C@@H:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][CH3:36])=[CH:28][CH:27]=3)[NH:22][C:21]2=[O:37])[C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[S:7][CH:8]=1)=[O:47])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11699649(2S,3S)-N-(4-Ethylsulfanyl-thiazol-2-yl)-2-{(R)-4-[4-(2-methoxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide

Product 1

HCID 11699779HCID 11699779, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(2S,3S)-N-(4-Ethylsulfanyl-thiazol-2-yl)-2-{(R)-4-[4-(2-methoxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (0.135 g, 0.24 mmole) (prepared as described in Example 16) was dissolved in anhydrous tetrahydrofuran (15 mL). To this solution was added a solution of m-chloroperbenzoic acid (0.066 g, 0.27 mmole) in tetrahydrofuran (8 mL). After stirring at room temperature for 30 minutes, the reaction was concentrated. The residue was dissolved in cold methylene chloride and washed twice with saturated sodium bicarbonate and twice with brine. Each aqueous phase was backwashed with a second portion of methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated. The crude material was purified by chromatography over silica gel eluted with a gradient of 50-100% v/v ethyl acetate in hexanes followed by 5% v/v methanol in ethyl acetate to yield (2S,3S)-N-(4-ethanesulfinyl-thiazol-2-yl)-2-{(R)-4-[4-(2-methoxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (0.103 g, 75%). This material was combined with another batch of material, dissolved in methylene chloride and added to hexanes to precipitate the product, (2S,3S)-N-(4-ethanesulfinyl-thiazol-2-yl)-2-{(R)-4-[4-(2-methoxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (0.117 g).

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutionThe residue was dissolved in cold methylene chloride
  3. washwashed twice with saturated sodium bicarbonate and twice with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography over silica gel
  7. washeluted with a gradient of 50-100% v/v ethyl acetate in hexanes

Sources & evidence

ORD record
ord-22ed5a2bdfc94f46b8270e8fb793be88
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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