HCID 70046131, compound → HCID 86748805, compound

HRID 1648120Notes

Reaction equation

HRID 1648120 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:22]([NH:24][CH:25]2[CH:29]([O:30]CC3C=CC=CC=3)[O:28][C:27](=[O:38])[CH2:26]2)=[O:23])[CH3:21])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])=[CH:4][CH:3]=1>CO.[OH-].[OH-].[Pd+2]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:22]([NH:24][CH:25]([CH:29]=[O:30])[CH2:26][C:27]([OH:38])=[O:28])=[O:23])[CH3:21])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70046131HCID 70046131, compound

Product 1

HCID 86748805HCID 86748805, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 195 mg of N-(3-(4-hydroxyphenyl)propionyl-valinyl-alaninyl)-4-amino-5-benzyloxy-2-oxotetrahydrofuran in 5 mL of methanol was added ~100 mg of Pd(OH)2 on carbon. After the mixture had been stirred vigorously under hydrogen for 3 hours, the mixture was filtered through a 0.22 μm nylon membrane filter and concentrated. The residue was purified by MPLC on silica-gel (22×300 mm column, eluted with a gradient of dichloromethane to 8% formic acid and 32% methanol in dichloromethane) to afford 115 mg of the title compound as a colorless solid: 1H NMR (400 MHz, CD3OD (1:1 mixture of diastereomeric hemiacetals in this solvent)) δ7.01 (d, 2H, J=8.39 Hz, Ar--H), 6.67 (d, 2H, J=8.53 Hz, Ar--H), 4.58 (d, 0.5H, J=3.92 Hz, CH(OH)(OCD3)), 4.56 (d, 0.5H, J=4.06 Hz, CH(OH)(OCD 3)), 4.34 (m, 1H, CHN), 4.24 (m, 1H, CHN), 4.09 (d, 1H, J=7.10 Hz, CHN), 2.81 (t, 2H, J=7.56 Hz, CH2CON), 2.7-2.4 (m, 4H, CH2Ar, CH2CO2), 2.00 (m, 1H, CH(CH3)2), 1.32 (d, 3H, J=5.81Hz, CHCH3), 0.89 (d, 3H, J=6.82 Hz, CH(CH3)2), 0.85 (d, 3H, J=6.87 Hz, CH(CH3)2).

Workup

  1. filtrationthe mixture was filtered through a 0.22 μm nylon membrane
  2. filtrationfilter
  3. concentrationconcentrated
  4. customThe residue was purified by MPLC on silica-gel (22×300 mm column
  5. washeluted with a gradient of dichloromethane to 8% formic acid and 32% methanol in dichloromethane)

Sources & evidence

ORD record
ord-21b6a0edc6074e8aae6ff230d4ef1e8a
Source dataset
uspto-grants-1995_07
Patent number
US05434248

Reaction notes

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