HCID 90052135, compound → HCID 90052139, compound

HRID 2284745Notes

Reaction equation

HRID 2284745 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]([NH:29]C(=O)OC(C)(C)C)([CH2:25][CH2:26][O:27][CH3:28])[CH2:6][NH:7][C:8](=[O:24])[O:9][CH2:10][CH:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:29][C:5]([CH2:4][CH2:3][O:2][CH3:1])([CH2:25][CH2:26][O:27][CH3:28])[CH2:6][NH:7][C:8](=[O:24])[O:9][CH2:10][CH:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

4

Reactant 1

HCID 90052135HCID 90052135, compound

Product 1

HCID 90052139HCID 90052139, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (9H-fluoren-9-yl)methyl tert-butyl (4-methoxy-2-(2-methoxyethyl)butane-1,2-diyl)dicarbamate (G22, 269 mg) in methylene chloride (2 mL), trifluoroacetic acid (2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 5 hours. The solvent was evaporated under reduced pressure, and then ethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the residue. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain (9H-fluoren-9-yl)methyl (2-amino-4-methoxy-2-(2-methoxyethyl)butyl)carbamate (G23, 186 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the residue
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8fb3067ae3704c8aab53cf040a854a02
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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