Water → HCID 68044574, compound

HRID 1524356Notes

Reaction equation

HRID 1524356 reaction equation
C[O:2][C:3](=O)[C@@H:4]([N:8]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[S:9]([C:12]1[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH2:5][CH:6]=[CH2:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[OH:17][CH2:16][C:15]1[CH:20]=[CH:21][C:12]([S:9]([N:8]([C@@H:4]([CH2:5][CH:6]=[CH2:7])[CH2:3][OH:2])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68044635HCID 68044635, compound

Product 1

HCID 68044574HCID 68044574, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the material from Step 1 (2 g, 5.03 mmol) in THF (33.5 mL) at 0° C. was slowly added 1.0 M lithium aluminum hydride (10 mL, 10.06 mmol). The reaction mixture was stirred at 0° C. for 20 minutes. Water (383 μL) was carefully added, followed by the slow addition of 15% NaOH (383 μL) and water (1.2 mL). The reaction mixture was vigorously stirred for 10 minutes. It was filtered through celite and washed with ether and EtOAc. The filtrate was concentrated in vacuo to afford 1.7 g of the title compound which was directly used at Step 2. LCMS (M+Na)=364.

Workup

  1. customat 0° C.
  2. stirringThe reaction mixture was vigorously stirred for 10 minutes
  3. filtrationIt was filtered through celite
  4. washwashed with ether and EtOAc
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c4e430763cc948dfbe75637e3611c733
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

Loading…