HCID 74326946, compound → HCID 24827765, compound

HRID 1009188Notes

Reaction equation

HRID 1009188 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[C:7]2[S:11][C:10](=[O:12])[N:9]([CH2:13][C:14]3([CH3:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:8]2=[O:21])=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25]>CO.[Pd]>[OH:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[N:9]([CH2:13][C:14]3([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[C:8]2=[O:21])=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25]

Participants

4

Reactant 1

HCID 74326946HCID 74326946, compound

Product 1

HCID 24827765HCID 24827765, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound 12 (20 mg) and Pd—C (40 mg) in methanol (5 mL) was stirred under hydrogen (50 psi) overnight, filtered, and concentrated to dryness under vacuum. The residue was purified by silica gel flash chromatography and re-crystallized with ethyl acetate-hexane (1:8), giving compound 20 (14 mg). 1H NMR (250 MHz, CDCl3) 0.81 (s, 3H), 1.16-1.59 (m, 10H), 3.13 (dd, 1H, J=9.3 Hz, 8.7 Hz), 3.45 (s, 2H), 3.51 (dd, 1H, J=9.3 Hz, 3.6 Hz), 4.44 (dd, 1H, J=3.6 Hz, 8.7 Hz), 5.53 (s, 1H), 6.92 (d, 1H, J=8.40 Hz), 7.33 (d, 1H, J=8.40 Hz), 7.39 (s, 1H), HRMS exact mass of (M+Na)+, 422.1170 amu; observed mass of (M+Na)+, 422.1173 amu.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness under vacuum
  3. customThe residue was purified by silica gel flash chromatography
  4. customre-crystallized with ethyl acetate-hexane (1:8)

Sources & evidence

ORD record
ord-19c5279865a14c2c9c6ca3b2c012c38e
Source dataset
uspto-grants-2011_07
Patent number
US07973062B2

Reaction notes

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