HCID 137194559, compound → HCID 136396957, compound

HRID 2110597Notes

Reaction equation

HRID 2110597 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:17][OH:18])([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:19])[C:3]=1[C:20]1[NH:25][C:24]2[CH:26]=[CH:27][C:28]([N:30]([CH2:35][C:36]([O:38]CC)=[O:37])[S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=2[S:22](=[O:42])(=[O:41])[N:21]=1>O1CCCC1.Cl>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:17][OH:18])([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C:4](=[O:19])[C:3]=1[C:20]1[NH:25][C:24]2[CH:26]=[CH:27][C:28]([N:30]([CH2:35][C:36]([OH:38])=[O:37])[S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=2[S:22](=[O:41])(=[O:42])[N:21]=1

Participants

4

Reactant 1

HCID 137194559HCID 137194559, compound

Product 1

HCID 136396957HCID 136396957, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 53B (15 mg, 0.024 mmol) in tetrahydrofuran (0.3 mL) and 1 N HCl (0.2 mL) was heated at 65° C. for 4 hours. The solution was cooled to room temperature and concentrated in vacuo. The residue was chromatographed on a reverse phase C18 column eluting with 5%-100% acetonitrile in water containing 0.1% trifluoroacetic acid to afforded the title compound as a yellow solid (4 mg, 28%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.46-0.61 (m, 1H), 0.67 (dd, J=12.50, 6.62 Hz, 6H, 0.93-1.05 (m, 1H), 1.16-1.40 (m, 1H), 1.69-1.90 (m, 1H), 1.96-2.16 (m, 1H), 3.11 (s, 3H), 4.46 (s, 2H), 7.43 (d, J=8.46 Hz, 1H), 7.56 (t, J=6.99 Hz, 1H), 7.61-7.73 (m, 2H), 7.73-7.91 (m, 2H), 8.16 (d, J=8.09 Hz, 1H), 10.45-10.75 (br.s, 1H), 12.91-13.14 (br.s, 1H), 14.50 (s, 1H); MS (ESI) m/z 593.0 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on a reverse phase C18 column
  3. washeluting with 5%-100% acetonitrile in water containing 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-1fec580235e849b7bcfcbdfdc0db32dd
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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