Triacetoxyperiodinane → HCID 71577130, compound

HRID 1025335Notes

Reaction equation

HRID 1025335 reaction equation
[CH:1]1([NH:4][C:5](=[O:37])[C@@H:6]([OH:36])[C@@H:7]([NH:10][C:11]([C@@H:13]2[CH2:17][C@@H:16]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=3[CH3:28])(=[O:20])=[O:19])[CH2:15][N:14]2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:12])[CH2:8][CH3:9])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1([NH:4][C:5](=[O:37])[C:6](=[O:36])[C@@H:7]([NH:10][C:11]([C@@H:13]2[CH2:17][C@@H:16]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=3[CH3:28])(=[O:19])=[O:20])[CH2:15][N:14]2[C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])=[O:12])[CH2:8][CH3:9])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 86762441HCID 86762441, compound

Product 1

HCID 71577130HCID 71577130, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-tert-butyl 2-((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxopentan-3-ylcarbamoyl)-4-(2,4-dimethylphenylsulfonyl)pyrrolidine-1-carboxylate (64 mg, 119 μmol, Eq: 1.00) and Dess-Martin periodinane (572 mg, 202 μmol, Eq: 1.7) were combined with CH2Cl2 (1 ml). The reaction was stirred overnight at RT. Dess-Martin periodinane (280 mg) was added again and stirred for 5 h, until near complete conversion. The reaction was extracted with 15 ml CH2Cl2 and 2×5 ml satd. Na2S2O3. The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by preparative HPLC. The title compound was obtained as a light yellow gum (52.5 mg, 82.3%, MS (m/e)=536.24 [M+H+]).

Workup

  1. stirringstirred for 5 h, until near complete conversion
  2. extractionThe reaction was extracted with 15 ml CH2Cl2 and 2×5 ml
  3. dry with materialThe organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-2074aec9e2724e24bdd6eaf866dd7d06
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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