Triacetoxyperiodinane → 5-Methoxy-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[(4S,6S)-6-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide

HRID 229789Notes

Reaction equation

HRID 229789 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][C:26]([O:29][CH3:30])=[CH:25][C:23]=3[CH:24]=2)=[O:19])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:7][CH:6]([CH3:31])[CH2:5][N:4]([S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)(=[O:34])=[O:33])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:15][CH:14]([CH3:16])[CH2:13][C@H:12]([NH:17][C:18]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:23]=2[CH:24]=1)=[O:19])[C:10](=[O:11])[NH:9][C@H:8]1[CH2:7][C@H:6]([CH3:31])[CH2:5][N:4]([S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)(=[O:34])=[O:33])[CH2:3][C:2]1=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 866074165-Methoxy-benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-6-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide

Product 1

HCID 98728245-Methoxy-benzofuran-2-carboxylic acid {(S)-3-methyl-1-[(4S,6S)-6-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-methoxy-benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-6-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide (110 mg, 0.19 mmol) in 5 ml CH2Cl2, was added Dess-Martin reagent (122 mg, 0.29 mmol) at RT. The solution was stirred for 2 h when 50 ml CH2Cl2 was added and then washed with 10% NaHCO3 and brine. Purification by column chromatograghy (50% ethyl acetate in hexane) gave the title compound (90 mg, 82% yield). 1H-NMR (400 Hz, CDCl3): d (ppm): 8.69(d, 1H), 7.94(m, 2H), 7.39-7.24(m, 3H), 7.02(m, 4H), 5.26(m, 1H), 4.69(m, 2H), 3.84(m, 4H), 3.00(m, 1H), 2.05(m, 1H), 1.73(m, 2H), 1.61(m, 4H), 1.18(d, 3H), 0.97(d,6H);). The diastereomers were separated by HPLC. Diastereomer 1: MS (M+H+): 571.2; Diastereomer 2: MS (M+H+): 571.2

Workup

  1. additionwas added
  2. washwashed with 10% NaHCO3 and brine
  3. customPurification by column chromatograghy (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bf562e58d95e4f129325f1743706807a
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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