Ammonium Chloride → HCID 54448701, compound

HRID 1782750Notes

Reaction equation

HRID 1782750 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([CH:35]=[C:36]([Br:39])[C:37]=1[OH:38])[CH2:11][C@H:12]([C:21]([N:23]1[CH2:28][CH2:27][CH:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:25][CH2:24]1)=O)[NH:13][C:14](OC(C)(C)C)=O.[Cl-].[NH4+]>O1CCCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH2:11][C@@H:12]([NH:13][CH3:14])[CH2:21][N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:25][CH2:24]2)[CH:35]=[C:36]([Br:39])[C:37]=1[OH:38]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 53914981HCID 53914981, compound

Product 1

HCID 54448701HCID 54448701, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2.3 g (60 mmol) lithium aluminium hydride in 100 ml anhydrous tetrahydrofuran, a solution of 11.0 g (18.66 mmol) 1-[3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-tyrosyl]-4-(1-piperidinyl)piperidine in 100 ml anhydrous tetrahydrofuran was added dropwise at room temperature whilst being stirred. It was stirred for a further 15 minutes at room temperature and then refluxed for 3 hours. 3 ml 20% aqueous ammonium chloride solution was added to the cooled mixture, then it was dried with magnesium sulphate. The filter cake was filtered and washed with 300 ml of an ethyl ethanoate-methanol mixture (1/1 v/v), and the combined filtrates were evaporated in a vacuum. The residue was purified by column chromatography over silica gel using ethyl ethanoate/methanol (8/2 v/v) for elution.

Workup

  1. stirringIt was stirred for a further 15 minutes at room temperature
  2. temperaturerefluxed for 3 hours
  3. dry with materialit was dried with magnesium sulphate
  4. filtrationThe filter cake was filtered
  5. washwashed with 300 ml of an ethyl ethanoate-methanol mixture (1/1 v/v)
  6. customthe combined filtrates were evaporated in a vacuum
  7. customThe residue was purified by column chromatography over silica gel
  8. washfor elution

Sources & evidence

ORD record
ord-81654d5a90fb4625848bcfd5d1a62659
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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