Hydrochloric Acid → HCID 68855063, compound

HRID 1782731Notes

Reaction equation

HRID 1782731 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([CH:28]=[C:29]([Br:32])[C:30]=1[OH:31])[CH2:11][C@H:12]([C:14]([N:16]1[CH2:21][CH2:20][CH:19]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:18][CH2:17]1)=O)[NH2:13].O.Cl>C1COCC1.CO>[NH2:13][C@H:12]([CH2:11][C:10]1[CH:28]=[C:29]([Br:32])[C:30]([OH:31])=[C:8]([Br:7])[CH:9]=1)[CH2:14][N:16]1[CH2:21][CH2:20][CH:19]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54024913HCID 54024913, compound

Product 1

HCID 68855063HCID 68855063, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3.8 g (100 mmol) of lithium aluminium hydride in 400 ml of THF were added in batches, with stirring and at room temperature, 14.4 g (20 mmol) of 1-(3,5-dibromo-D-tyrosyl)-4-(1-piperidinyl)-piperidine within 30 minutes. The reaction mixture was kept for 30 minutes at room temperature and refluxed for 2 hours and then neutralised by the careful addition of 1 ml of water and 5.1 ml of concentrated aqueous hydrochloric acid. After the addition of 100 ml of methanol the solid precipitate was suction filtered and the filtrate was evaporated down in vacuo. The residue was purified by column chromatography (MN-silica gel 60, Macherey-Nagel, 70-230 mesh ASTM, eluant: methylene chloride/methanol/conc. aqueous ammonia=8/2/0.2 (v/v/v)). 5.4 g (57% of theory) of the desired product was obtained as an amorphous solid.

Workup

  1. additionwere added in batches
  2. temperaturerefluxed for 2 hours
  3. filtrationfiltered
  4. customthe filtrate was evaporated down in vacuo
  5. customThe residue was purified by column chromatography (MN-silica gel 60, Macherey-Nagel, 70-230 mesh ASTM, eluant: methylene chloride/methanol/conc. aqueous ammonia=8/2/0.2 (v/v/v))

Sources & evidence

ORD record
ord-4a7e541d464a41509c2c63f3d0e4e9e2
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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