Triacetoxyperiodinane → N-[(5-fluoro-1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

HRID 634952Notes

Reaction equation

HRID 634952 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([NH:14][C@H:15]([C:19]([NH:21][CH:22]([CH:31]([OH:44])[CH2:32][O:33][C:34]1[C:39]([F:40])=[C:38]([F:41])[CH:37]=[C:36]([F:42])[C:35]=1[F:43])[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])=[CH:5]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([NH:14][C@H:15]([C:19]([NH:21][CH:22]([C:31](=[O:44])[CH2:32][O:33][C:34]1[C:39]([F:40])=[C:38]([F:41])[CH:37]=[C:36]([F:42])[C:35]=1[F:43])[CH2:23][C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[O:20])[CH:16]([CH3:17])[CH3:18])=[O:13])=[CH:5]2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86756374N-[(5-fluoro-1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

Product 1

HCID 86756373N-[(5-fluoro-1-methyl-indole-2-cabonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic Acid, tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(5-fluoro-1-methyl-indole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (112.6 mg, 0.18 mmol) in CH2Cl2 (5.0 ml) was added Dess-Martin periodinane (95 mg, 0.22 mmol) and the solution stirred for 10 min. at room temperature. The reaction was quenched with Na2S2O4, diluted with EtOAc, washed with NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacito. The crude product was purified by chromatography (1:1 EtOAc/hexane) to give the titled product as a white solid (which was directly taken to the next step in Example 115).

Workup

  1. customThe reaction was quenched with Na2S2O4
  2. additiondiluted with EtOAc
  3. washwashed with NaHCO3, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacito
  7. customThe crude product was purified by chromatography (1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-e5a75e4d733f4507a4e057900eff9dad
Source dataset
uspto-grants-2001_02
Patent number
US06184244B2

Reaction notes

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