Hydrochloric Acid → HCID 57114887, compound

HRID 1351892Notes

Reaction equation

HRID 1351892 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-1ac2766e93154d61a5c4d6ac644d674e
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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