Water → HCID 58392391, compound

HRID 561603Notes

Reaction equation

HRID 561603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH3:26])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][C:10](OCC)=[O:11])=[CH:4][C:3]=1[F:27].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(#N)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH3:26])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:10][OH:11])=[CH:4][C:3]=1[F:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 21226445Aluminium lithium hydrideHCID 58392178HCID 58392178, compound

Product 1

HCID 58392391HCID 58392391, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of 1.74 g (4.28 mmol) of the compound from Example 101A in 7 ml of tetrahydrofuran was added dropwise to 15.0 ml (15.05 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 20 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). 1.36 g (87% 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-6a38021ad4d448c79a4567668c35f5f2
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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