Hydrochloric Acid → HCID 45280222, compound

HRID 422875Notes

Reaction equation

HRID 422875 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[C:12]3([CH2:28][O:29][C:8]=2[CH:7]=1)[C:20]1[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[N:14]([CH2:21][C@H:22]1[CH2:26][CH2:25][CH2:24][O:23]1)[C:13]3=[O:27].[OH-].[Li+].Cl>O1CCCC1.O>[O:27]=[C:13]1[C:12]2([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:30])=[O:2])=[CH:7][C:8]=3[O:29][CH2:28]2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]1[CH2:21][C@H:22]1[CH2:26][CH2:25][CH2:24][O:23]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58260011HCID 58260011, compound

Product 1

HCID 45280222HCID 45280222, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl({2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl}oxy)acetate (0.51 g, 1.25 mmol) in tetrahydrofuran (4 mL) and water (1 mL) was added lithium hydroxide (0.05 g, 1.62 mmol). The reaction mixture was stirred at ambient temperature for 16 h. To the reaction mixture was added 1 N HCl to adjust pH<2, then extracted with ethyl acetate (2×50 mL). The combined organic solution was washed with water and brine, then dried over sodium sulfate, filtered and concentrated to afford ({2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indol]-6-yl}oxy)acetic acid (0.42 g, 85%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.33-7.26 (m, 1H), 7.15-7.00 (m, 3H), 6.64 (d, J=8.4 Hz, 1H), 6.54 (d, J=2.4 Hz, 1H), 6.40-6.34 (m, 1H), 4.96 (d, J=9.0 Hz, 1H), 4.70 (d, J=9.0 Hz, 1H), 4.59 (s, 2H), 4.35-4.24 (m, 1H), 3.99-3.68 (m, 4H), 2.10-1.86 (m, 3H), 1.79-1.65 (m, 1H); MS (ES+) m/z 396.0 (M+1), 417.9 (M+23).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic solution was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-448e5d2877984e3eb22b10586fafdaec
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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