HCID 67980106, compound → HCID 67980047, compound

HRID 2367940Notes

Reaction equation

HRID 2367940 reaction equation
C([O:4][C@@H:5]1[C@@H:33]([N:34]2[CH:38]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[F:45])[N:36]=[N:35]2)[C@@H:32]([O:46]C(=O)C)[C@@H:31]([CH2:50][O:51]C(=O)C)[O:30][C@H:6]1[S:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[N:16]=[N:15]2)[C@H:9]1[O:26]C(=O)C)(=O)C>C[O-].[Na+]>[F:45][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[C:37]1[N:36]=[N:35][N:34]([C@H:33]2[C@@H:32]([OH:46])[C@@H:31]([CH2:50][OH:51])[O:30][C@@H:6]([S:7][C@@H:8]3[CH2:13][CH2:12][CH2:11][C@H:10]([N:14]4[CH:18]=[C:17]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=5[F:25])[N:16]=[N:15]4)[C@H:9]3[OH:26])[C@@H:5]2[OH:4])[CH:38]=1

Participants

3

Reactant 1

HCID 67980106HCID 67980106, compound

Product 1

HCID 67980047HCID 67980047, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Compound 10 (12.0 mg, 15.6 μmol) was dissolved in NaOMe (0.05 M, 1 mL). After 21 h the mixture was neutralized (Duolite C436) and concentrated. Purification was made by reverse-phase HPLC using a linear gradient of H2O:MECN (100%->0% H2O). The reaction yielded 55% of 15. 1H-NMR (MeOD) 8.38 (d, J=3.53 Hz, 1 H), 8.35 (d, J=3.55 Hz, 1 H), 8.08-8.18 (m, 2 H), 7.33-7.43 (m, 2 H), 7.18-7.33 (m, 4 H), 4.92 (dd, 1 H), 4.76 (d, 9.48 Hz, 1 H), 4.47-4.57 (m, 1 H), 4.28 (dd, J=9.51, 10.55 Hz, 1 H), 4.15 (d, J=2.98 Hz, 1 H), 3.83-3.93 (m, 2 H), 3.76 (dd, J=6.87, 11.35 Hz, 1 H), 3.68 (dd, J=5.19, 11.37 Hz, 1 H), 3.07-3.17 (m, 1 H), 2.28-2.38 (m, 1 H), 2.08-2.25 (m, 2 H), 1.90-2.00 (m, 1 H), 1.60-1.77 (m, 2 H).

Workup

  1. concentration(Duolite C436) and concentrated
  2. customPurification

Sources & evidence

ORD record
ord-f0e1a43ccafc4ed481dd86e7c56b8722
Source dataset
uspto-grants-2014_04
Patent number
US08703720B2

Reaction notes

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