Phenol → HCID 69917637, compound

HRID 2307799Notes

Reaction equation

HRID 2307799 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](F)[CH:20]=2)[CH:16]=1)(C)(C)C.[C:37]1([OH:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[OH-].[K+]>>[NH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]([CH2:26][C@H:8]([NH2:7])[CH2:9][O:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([O:43][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH:20]=3)[CH:16]=2)=[CH:28]1

Participants

4

Reactant 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 69917639HCID 69917639, compound

Product 1

HCID 69917637HCID 69917637, compoundYield 9.3%

Procedure

A mixture of Example 216B (50 mg, 0.1 mmol), phenol (94 mg, 1.0 mmol) and KOH (11.2 mg, 0.2 mmol) was heated at 140 C in a sealed bottle for 2 hrs. The mixture was concentrated to dryness. The residue was then treated with TFA (1 mL) at rt for 10 min. Upon Removal of TFA, the crude product was purified on C18 HPLC to give rhe title compound (4.3 mg, 5.3%). MS (DCI/NH3) m/z 463 (M+1)+; 1HNMR (400 MHz, MeOD) δ ppm 3.30 (m, 1 H) 3.48 (dd, J=13.81, 7.06 Hz, 1 H) 4.00 (m, 1 H) 4.27 (dd, J=10.43, 5.83 Hz, 1 H) 4.40 (dd, J=10.43, 3.07 Hz, 1 H) 7.15-7.01 (m, 5H) 7.26-7.23 (m, 2H) 7.48-7.32 (m, 6H) 7.59 (d, J=7.98 Hz, 1 H) 7.87 (m, 1 H) 8.16 (d, J=5.52 Hz, 1 H) 8.35 (s, 1 H) 8.53 (s, 1 H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additionThe residue was then treated with TFA (1 mL) at rt for 10 min
  3. customUpon Removal of TFA
  4. customthe crude product was purified on C18 HPLC

Sources & evidence

ORD record
ord-574c6192a41c43aaa8288e6ad21158b7
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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