Water → HCID 71556980, compound

HRID 1024033Notes

Reaction equation

HRID 1024033 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26]2[N:27]=[C:28]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([N:42]4[CH2:47][CH2:46][N:45]([CH:48]5[CH2:51][O:50][CH2:49]5)[CH2:44][CH2:43]4)=[CH:38][N:37]=3)[C:29]3[N:30]([CH:32]=[CH:33][N:34]=3)[CH:31]=2)[C:5]([CH2:22]C(=O)C)=[C:6]([N:8]2[CH2:20][CH2:19][N:11]3[C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[CH:18]=[C:10]3[C:9]2=[O:21])[CH:7]=1.[OH2:52].[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:26]2[N:27]=[C:28]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([N:42]4[CH2:47][CH2:46][N:45]([CH:48]5[CH2:49][O:50][CH2:51]5)[CH2:44][CH2:43]4)=[CH:38][N:37]=3)[C:29]3[N:30]([CH:32]=[CH:33][N:34]=3)[CH:31]=2)[C:5]([CH2:22][OH:52])=[C:6]([N:8]2[CH2:20][CH2:19][N:11]3[C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[CH:18]=[C:10]3[C:9]2=[O:21])[CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium HydroxideHCID 86684130HCID 86684130, compound

Product 1

HCID 71556980HCID 71556980, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100-mL single-neck round-bottomed flask was charged with 107a (150 mg, 0.21 mol) in THF/iPA/H2O (5 mL/5 mL/2 mL) and LiOH (85 mg, 3.5 mmol) while stirring. This mixture was stirred at 50° C. for 0.5 h. Then 20 mL H2O was added and the mixture was extracted with EA (30 mL×3). The combined organic layer was dried over Na2SO4 and concentrated to give a yellow solid, which was further purified by reverse-phase prep-HPLC to afford 107 as a white solid (74 mg, 52% yield). LCMS: [M+H]+ 664.3. 1H NMR (500 MHz, DMSO) δ 9.06 (s, 1H), 8.41 (s, 1H), 8.13-8.10 (m, 2H), 7.98 (d, J=2.5, 1H), 7.71 (s, 1H), 7.48-7.44 (m, 2H), 7.39-7.36 (m, 1H), 6.54 (s, 1H), 5.38 (m, 1H), 4.57-4.35 (m, 6H), 4.18-4.13 (m, 4H), 3.44-3.42 (m, 1H), 3.15 (s, 4H), 2.59 (d, J=3.0, 2H), 2.47-2.40 (m, 6H), 1.79-1.69 (m, 4H)

Workup

  1. stirringThis mixture was stirred at 50° C. for 0.5 h
  2. extractionthe mixture was extracted with EA (30 mL×3)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give a yellow solid, which
  6. customwas further purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-1ccc82f18b594f2786520783a26501d4
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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