Hydrochloric Acid → HCID 58392262, compound

HRID 561519Notes

Reaction equation

HRID 561519 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:16]1[C:24]2[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1)[CH2:10][C:11](OCC)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:16]1[C:24]2[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1)[CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 58392496HCID 58392496, compound

Product 1

HCID 58392262HCID 58392262, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2.34 g (5.54 mmol) of the compound from Example 38A in 20 ml of tetrahydrofuran was added dropwise to 19.4 ml (19.4 mmol) of a 1N solution of lithium aluminum hydride in tetrahydrofuran in 50 ml of tetrahydrofuran at RT under argon. The mixture was stirred at RT for 15 min and then 1N hydrochloric acid was added. The mixture was extracted with dichloromethane, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 2.00 g (95% of theory) of the title compound.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-f21b8a20d7504c5ba1e75054688e66a2
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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