Hydrochloric Acid → HCID 69330911, compound

HRID 1351899Notes

Reaction equation

HRID 1351899 reaction equation
[OH:1][CH2:2][C:3]1[CH:39]=[CH:38][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([N:12](C(OC(C)(C)C)=O)[CH2:13][C@H:14]([O:23][Si](CC)(CC)CC)[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][C:5]=2[CH:4]=1.[ClH:40]>C(OCC)(=O)C>[ClH:40].[OH:1][CH2:2][C:3]1[CH:39]=[CH:38][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([NH:12][CH2:13][C@H:14]([OH:23])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56983775HCID 56983775, compound

Product 1

HCID 69330911HCID 69330911, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To N-(3-hydroxymethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethyl-silyloxy)propyl]-tert-butoxycarbonylamine (200 mg) was added 4N hydrogen chloride in ethyl acetate (6 ml) at room temperature, and the mixture was stirred at the same temperature for 1 hour. After evaporation in vacuo, the residue was dissolved into a mixture of saturated aqueous sodium hydrogencarbonate and ethyl acetate. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (silica gel, chloroform:methanol=5:1) and followed by treatment with 4N hydrogen chloride in ethyl acetate to give (2S)-1-(3-hydroxymethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino-3-phenoxy-2-propanol hydrochloride (45 mg).

Workup

  1. customAfter evaporation in vacuo
  2. dissolutionthe residue was dissolved into a mixture of saturated aqueous sodium hydrogencarbonate and ethyl acetate
  3. customAfter separation
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin layer chromatography (silica gel, chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-84b7cf5b7eeb49de831636ac0820492a
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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