Triacetoxyperiodinane → HCID 86586128, compound

HRID 751468Notes

Reaction equation

HRID 751468 reaction equation
[OH:1][CH:2]1[CH:8]([NH:9][C:10]([C@@H:12]([NH:17][C:18]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[CH:24]=2)=[O:19])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:7][C:6]([CH3:30])([CH3:29])[CH2:5][N:4]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)(=[O:33])=[O:32])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[CH:8]([NH:9][C:10]([C@@H:12]([NH:17][C:18]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[CH:24]=2)=[O:19])[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:11])[CH2:7][C:6]([CH3:29])([CH3:30])[CH2:5][N:4]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)(=[O:32])=[O:33])[CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86586127HCID 86586127, compound

Product 1

HCID 86586128HCID 86586128, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-6,6-dimethyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide from Example 92i (100 mg, 0.18 mmol) in 2 ml CH2Cl2, was added Dess-Martin reagent (76 mg, 0.18 mmol) at r.t. The solution was stirred for 2 h when 20 ml CH2Cl2 was added and then washed with NaHCO3 and brine. Purification by column chromatograghy (50% ethyl acetate in hexane) gave 70 mg of the title compound in 70% yield. MS (M+H+): 555.4; 1H-NMR (400 MHz, CDCl3): •8.68-8.67(d, 1H), 7.97-7.93(m, 2H), 7.69-7.28(m, 6H), 7.32-6.92(m, 2H), 5.24(m, 1H), 4.79-4.69(m, 2H), 3.80-3.71(m, 2H), 2.54-2.50(d, 1H), 1.92-1.76(m, 4H), 1.45-1.40(m, 4H), 1.01-0.91(m, 9H).

Workup

  1. additionwas added
  2. washwashed with NaHCO3 and brine
  3. customPurification by column chromatograghy (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-39ac1cc5186844dab9583b39303ae828
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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