Hydrochloric Acid → HCID 69917655, compound

HRID 2307824Notes

Reaction equation

HRID 2307824 reaction equation
C[O:2][C:3](=O)[C@@H:4]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:13]=2)[NH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.Cl>C1COCC1.CO>[C:27]([O:26][C:24](=[O:25])[NH:23][C@H:4]([CH2:3][OH:2])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:13]=2)[NH:8][CH:7]=1)([CH3:28])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 69918141HCID 69918141, compound

Product 1

HCID 69917655HCID 69917655, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 400B (1.50 g, 3.3 mmol) in THF (15 mL) was slowly added LiAlH4 powder (127 mg, 3.3 mmol) in several portion at rt. After the addition, the reaction mixture was becoming sticky and the stirring stopped. The temperature of the mixture arises to ˜50° C. Ether (30 mL) was added and the mixture was stirred for 20 min. Methanol (2 mL) and diluted HCl was added slowly and the mixture was extracted with ether. The organic phase was washed with water and concentrated. The residue was separated by flash chromatography (20-60% EtOAc in hexane) to give the desired product (982 mg, 70%). MS (DCI) m/z 421 (M+1)+.

Workup

  1. customat rt
  2. additionAfter the addition
  3. customarises to ˜50° C
  4. extractionthe mixture was extracted with ether
  5. washThe organic phase was washed with water
  6. concentrationconcentrated
  7. customThe residue was separated by flash chromatography (20-60% EtOAc in hexane)

Sources & evidence

ORD record
ord-45b8c9c878eb43e2b8c8e962beb65458
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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