Methyl morpholine oxide → (3RS)-3-[N-((1-Naphthyloxy)Acetyl)Valinyl]Amino-5-Fluoro-4-Oxopentanoic Acid, tert-Butyl Ester

HRID 1371289Notes

Reaction equation

HRID 1371289 reaction equation
[C:1]1([O:11][CH2:12][C:13]([NH:15][C@H:16]([C:20]([NH:22][CH:23]([CH:32]([OH:35])[CH2:33][F:34])[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]1([O:11][CH2:12][C:13]([NH:15][C@H:16]([C:20]([NH:22][CH:23]([C:32](=[O:35])[CH2:33][F:34])[CH2:24][C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])=[O:21])[CH:17]([CH3:18])[CH3:19])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86585454(3RS,4RS)-3-[N-((1-Naphthyloxy)Acetyl)Valinyl]Amino-5-Fluoro-4-Hydroxypentanoic Acid, tert-Butyl Ester

Product 1

HCID 86585455(3RS)-3-[N-((1-Naphthyloxy)Acetyl)Valinyl]Amino-5-Fluoro-4-Oxopentanoic Acid, tert-Butyl EsterYield 80.6%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3RS,4RS)-3-[N-((1-naphthyloxy)acetyl)valinyl]amino-5-fluoro-4-hydroxypentanoic acid, tert-butyl ester (0.163 g, 0.315 mmol) and N-methylmorpholine N-oxide (0.144 g, 0.98 mmol) in CH2Cl2 (5.0 mL) at room temperature was added activated 4 Å molecular sieves. After stirring at room temperature for 20 min, the mixture was treated with tetra(n-propyl)ammonium perruthenate (0.011 g). After stirring at room temperature for 3.5 hrs, the mixture through Celite and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with EtOAc-hexane (3:4) to give the title compound (0.124 g, 40%) as a pale yellow oil. TLC(MeOH-CH2Cl2; 1:9) Rf=0.71. 1H NMR (CDCl3): δ 8.27–8.23 (m, 1H), 7.86–7.83 (m, 1H), 7.59–7.51 (m, 3H), 7.42–7.36 (m, 1H), 7.23–7.19 (m, 1H), 7.05–6.95 (m, 1H), 6.84 (d, 1H, J=7.7 Hz), 5.26–4.97 (m, 2H), 4.93–4.89 (m, 1H), 4.76 (s, 2H), 4.45–4.35 (m, 1H), 3.05–2.76 (m, 2H), 1.42 (d, 9H, J=4.1 Hz), 1.02–0.87 (m, 6H).

Workup

  1. stirringAfter stirring at room temperature for 3.5 hrs
  2. customthe mixture through Celite and evaporated to dryness
  3. customThe residue was purified by flash chromatography on silica gel eluting with EtOAc-hexane (3:4)

Sources & evidence

ORD record
ord-9cafc48bf22943a998eb4512cfc7aafb
Source dataset
uspto-grants-2007_01
Patent number
US07157430B2

Reaction notes

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