Triacetoxyperiodinane → HCID 131730334, compound

HRID 1948326Notes

Reaction equation

HRID 1948326 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([CH2:23][OH:24])[N:22]=2)[CH2:14][C@H:13]1[O:30][CH3:31])=[O:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([CH:23]=[O:24])[N:22]=2)[CH2:14][C@H:13]1[O:30][CH3:31])=[O:10]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131730335HCID 131730335, compound

Product 1

HCID 131730334HCID 131730334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Cis(±)-ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate (0.63 g, 1.3 mmol, Example 143) in methylene chloride was added Dess-Martin periodinane (0.61 g, 1.4 mmol). After 1 hr stirring at room temperature the reaction was complete. The crude reaction mixture was washed with water (×2) and brine, followed by drying with MgSO4 and concentrating to a minimal volume of methylene chloride after which it was directly deposited on a silica gel flash column (gradient elution to 1:1 EtOAc in CH2 Cl2). Pure fractions concentrated to clean, yellow solid (0.56 g). NMR: 1.29 (t, 3 H) 1.75 (s, 2 H) 2.18 (s, 3 H) 3.38 (s, 4 H) 3.44 (s, 1 H) 3.57 (s, 1 H) 4.03 (d, 1H) 4.22-4.35 (m, 4 H) 7.15 (d, 1 H) 10.31 (s, 1 H) 12.16 (s, 1 H).

Workup

  1. customThe crude reaction mixture
  2. washwas washed with water (×2) and brine
  3. dry with materialby drying with MgSO4
  4. concentrationconcentrating to a minimal volume of methylene chloride after which it
  5. washwas directly deposited on a silica gel flash column (gradient elution to 1:1 EtOAc in CH2 Cl2)
  6. concentrationPure fractions concentrated

Sources & evidence

ORD record
ord-f3964a44ed194e89969cce61afe01f39
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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