Water → HCID 58118671, compound

HRID 1615840Notes

Reaction equation

HRID 1615840 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:26][C:25]1[C:20](=[CH:21][CH:22]=[C:23]([SH-:27]C(=S)OCC)[CH:24]=1)[CH2:19]2.[OH-].[Na+].O>CCO>[SH:27][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[CH2:19][C@:3]1([C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[C:2]1=[O:1])[CH2:26]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 178473697HCID 178473697, compound

Product 1

HCID 58118671HCID 58118671, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of O-ethyl S-[(2R)-2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-yl]carbonodithioate from Step B (740 mg, 1.52 mmol) in EtOH (4 mL) was added 1 N NaOH (3.0 mL, 3.0 mmol). The resulting suspension was heated at 60° C. for 90 min, then cooled and poured into H2O (50 mL). The mixture was extracted with EtOAc (2×70 mL), and the combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated in vacuo to yield the title compound. MS: m/z=462 (M+Na+CH3CN).

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with EtOAc (2×70 mL)
  3. washthe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5c9b6502cbf43eeb693138959d837e0
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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