Triacetoxyperiodinane → (4S,5R)-tert-Butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-formyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 660389Notes

Reaction equation

HRID 660389 reaction equation
[CH3:1][C:2]([CH3:32])([CH2:28][CH2:29][CH2:30][CH3:31])[C:3]([NH:5][CH2:6][C@H:7]1[O:11][C:10]([CH3:13])([CH3:12])[N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:8]1[CH2:21][C@H:22]([CH2:26][OH:27])[CH:23]([CH3:25])[CH3:24])=[O:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:32][C:2]([CH3:1])([CH2:28][CH2:29][CH2:30][CH3:31])[C:3]([NH:5][CH2:6][C@H:7]1[O:11][C:10]([CH3:12])([CH3:13])[N:9]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@H:8]1[CH2:21][C@H:22]([CH:26]=[O:27])[CH:23]([CH3:24])[CH3:25])=[O:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68784232(4S,5R)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxymethyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 86649363(4S,5R)-tert-Butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-formyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4S,5R)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxymethyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (100 mg, 0.22 mmol) in anhydrous CH2Cl2 (5 mL) was added Dess-Martin reagent (120 mg, 0.283 mmol). The reaction mixture was stirred at rt for 5 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to (4S,5R)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-formyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (80 mg, 80%), which was used without purification; MS: 455 (M++1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure to (4S,5R)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-formyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (80 mg, 80%), which
  3. customwas used without purification

Sources & evidence

ORD record
ord-3614f4d2a0c24e658f2e8c5c4adaade2
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

Loading…