Water → HCID 58392513, compound

HRID 561605Notes

Reaction equation

HRID 561605 reaction equation
[F:1][C:2]1([F:30])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]([C:18]3[C:26]4[C:21](=[C:22]([CH2:27][S:28][CH3:29])[CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:12][C:13](OCC)=[O:14])=[CH:10][C:4]=2[O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(#N)C>O1CCCC1>[F:30][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]([C:18]3[C:26]4[C:21](=[C:22]([CH2:27][S:28][CH3:29])[CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:12][CH2:13][OH:14])=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 21226445Aluminium lithium hydrideHCID 58392094HCID 58392094, compound

Product 1

HCID 58392513HCID 58392513, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of 1.67 g (3.86 mmol) of the compound from Example 103A in 8 ml of tetrahydrofuran was added dropwise to 13.5 ml (13.5 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 16 ml of tetrahydrofuran at RT under argon. The mixture was stirred at 60° C. for 1 h and then water and acetonitrile were added, and the suspension was filtered through kieselguhr. The solvents were removed in a rotary evaporator, and the residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 1.39 g (92% of theory) of the title compound were obtained.

Workup

  1. filtrationthe suspension was filtered through kieselguhr
  2. customThe solvents were removed in a rotary evaporator
  3. customthe residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-c0053f7b23424317bf48f9c4cbbc1b16
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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