Triacetoxyperiodinane → HCID 54430964, compound

HRID 751471Notes

Reaction equation

HRID 751471 reaction equation
[OH:1][CH:2]1[CH:8]([NH:9][C:10](=[O:28])[C@@H:11]([NH:16][C:17](=[O:27])[CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:6][CH2:5][N:4]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([S:29]([N:4]2[CH2:5][CH2:6][CH2:7][CH:8]([NH:9][C:10](=[O:28])[C@@H:11]([NH:16][C:17](=[O:27])[CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2](=[O:1])[CH2:3]2)(=[O:31])=[O:30])=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86586131HCID 86586131, compound2×

Product 1

HCID 54430964HCID 54430964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-2-(2-Benzyloxy-acetylamino)-4-methyl-pentanoic acid [3-hydroxy-1-(4-methoxy-benzenesulfonyl)-azepan-4-yl]-amide (compound 207c, 0.24 g, 0.44 mmol) was dissolved in CH2Cl2 (5 ml), then Dess-Martin periodinane (0.3 g, 0.7 mmol) was added and the reaction was stirred for 30 min. The reaction was diluted with CH2Cl2 (20 ml), then was extracted with aqueous 10% Na2S2O5 (10 ml), then aqueous 10% NaHCO3 (10 ml), water (10 ml), brine (10 ml). The combined organics were concentrated in vacuo. The residue was purified by HPLC (50:50 Ethanol:hexanes, 20 mL/min, 25 min, WhelkO-1(R,R) 21×250 mm column, UV detection at 280 nm and 305 nm) to yield the first elution as a white solid (47 mg, 43%): MS 560.4 (M+H+). 1H NMR (400 Hz,CDCl3): δ 7.73 (d, 2H), 7.40-7.30 (m, 5H), 7.05 (d, 2H), 3.99 (s, 2H), 3.88 (s, 3H), 2.28-2.10 (m, 2H), 0.95 (t, 6H), and second eluting diastereomer: MS 560.2 (M+H+).

Workup

  1. extractionwas extracted with aqueous 10% Na2S2O5 (10 ml)
  2. concentrationThe combined organics were concentrated in vacuo
  3. customThe residue was purified by HPLC (50:50 Ethanol:hexanes, 20 mL/min, 25 min, WhelkO-1(R,R) 21×250 mm column, UV detection at 280 nm and 305 nm)
  4. customto yield
  5. washthe first elution as a white solid (47 mg, 43%)

Sources & evidence

ORD record
ord-7e4eb48a058444ada2f9a14316a79623
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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