Sodium Hydroxide → HCID 71547124, compound

HRID 1403705Notes

Reaction equation

HRID 1403705 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:28](=[O:29])[C:20]=2[C:19]2[C:14](=[CH:15][C:16]([NH:30][CH2:31][C:32]([O:34]CC)=[O:33])=[CH:17][CH:18]=2)[C:13]1=[O:37])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:28](=[O:29])[C:20]=2[C:19]2[C:14](=[CH:15][C:16]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:17][CH:18]=2)[C:13]1=[O:37])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71546983HCID 71546983, compound

Product 1

HCID 71547124HCID 71547124, compoundYield 785.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The ester 39 (0.1 g, 0.02 mmol) was dissolved in MeOH-THF (10+10 mL) and aq NaOH (4 N, 5 mL) was added at room temperature. The reaction mixture was stirred at room temperature for 4 h. The solvent was removed on a rotary evaporator and the residue washed with 1 N HCl (30 mL) and extracted with CHCl3 (2×50 mL). The extract was dried over Na2SO4 and concentrated to afford pure 42 (0.075 g, 80%) which was obtained as a brown solid: mp 190-192° C. IR (KBr) 3350, 2973, 1692, 1645, 1619, 1578, 1520, 1364, 1164, 666 cm−1; 1H NMR (DMSO-d6, 300 MHz) δ 8.30 (d, J=8.7 Hz, 1 H), 7.59 (m, 1 H), 7.45 (m, 2 H), 7.39 (m, 1 H), 7.21 (dd, J=2.4, J=8.7 Hz, 1 H), 7.12 (d, J=2.4 Hz, 1 H), 7.07 (m, 1 H), 4.40 (m, 2 H), 3.90 (s, 2 H), 3.09 (m, 2 H), 1.86 (m, 2 H), 1.33 (s, 9 H); ESIMS (m/z, relative intensity) 500 (MNa+, 100); HRESIMS calcd for C26H27N3O6Na 500.1798 (MNa+), found 500.1806 (MNa+); HPLC purity: 95.5% (MeOH—H2O, 75:25).

Workup

  1. customThe solvent was removed on a rotary evaporator
  2. washthe residue washed with 1 N HCl (30 mL)
  3. extractionextracted with CHCl3 (2×50 mL)
  4. dry with materialThe extract was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8cefd6bb524847e0af8b7385cf1f4254
Source dataset
uspto-grants-2014_12
Patent number
US08912213B2

Reaction notes

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