Trifluoroacetic acid → Benzyl 2-(4-((((2R,4S)-4-amino-2-hydroxy-2,6-dimethyl-3-oxoheptyl)oxy)sulfonyl)-3,5-dimethylphenoxy)acetate

HRID 628157Notes

Reaction equation

HRID 628157 reaction equation
C(OC([NH:8][C@@H:9]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:10](=[O:39])[C@@:11]([OH:38])([CH3:37])[CH2:12][O:13][S:14]([C:17]1[C:34]([CH3:35])=[CH:33][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[CH:19][C:18]=1[CH3:36])(=[O:16])=[O:15])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@@H:9]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:10](=[O:39])[C@@:11]([OH:38])([CH3:37])[CH2:12][O:13][S:14]([C:17]1[C:34]([CH3:35])=[CH:33][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])=[CH:19][C:18]=1[CH3:36])(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86715366Benzyl 2-(4-((((2R,4S)-4-((tert-butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl)oxy)sulfonyl)-3,5-dimethylphenoxy)acetate

Product 1

HCID 86715368Benzyl 2-(4-((((2R,4S)-4-amino-2-hydroxy-2,6-dimethyl-3-oxoheptyl)oxy)sulfonyl)-3,5-dimethylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Referring to FIG. 37, to a solution of benzyl 2-(4-((((2R,4S)-4-((tert-butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl)oxy)sulfonyl)-3,5-dimethylphenoxy)acetate (540 mg, 0.87 mmol) in DCM (15 mL) was added TFA (5 mL). The reaction mixture was stirred at room temperature for 3 h. Removal of the solvent under reduced pressure gave product, which was used directly in the next step without further purification. LC-MS analysis confirmed the structure.

Workup

  1. customRemoval of the solvent under reduced pressure
  2. customgave product, which
  3. customwas used directly in the next step without further purification

Sources & evidence

ORD record
ord-3d1b2ea3e2bb4204b9c15abb1ce45833
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

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