Hydrochloric Acid → HCID 57114887, compound

HRID 2299679Notes

Reaction equation

HRID 2299679 reaction equation
[F:1][CH2:2][O:3][C:4]1[CH:33]=[CH:32][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]([N:13](C(OC(C)(C)C)=O)[CH2:14][C@H:15]([OH:24])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][C:6]=2[CH:5]=1.Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[F:1][CH2:2][O:3][C:4]1[CH:33]=[CH:32][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]([NH:13][CH2:14][C@H:15]([OH:24])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2×HCID 56978727HCID 56978727, compound

Product 1

HCID 57114887HCID 57114887, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of N-(3-fluoromethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-2-hydroxy-3-phenoxypropyl]-tert-butoxycarbonylamine (41 mg) in ethyl acetate (2 ml) was added 4N hydrogen chloride in ethyl acetate (0.45 ml) at room temperature, and the mixture was stirred at the same temperature for 5.5 hours. The mixture was poured into a mixture of saturated aqueous sodium hydrogencarbonate and ethyl acetate, followed by being made basic with saturated aqueous sodium hydrogencarbonate. After separation, the organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (silica gel, chloroform:methanol=10:1) to give (2S)-1-(3-fluoromethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino-3-phenoxy-2-propanol (23 mg).

Workup

  1. customAfter separation
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (silica gel, chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-0fed51ccd61d47e2bafef8784448bcb6
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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