Trifluoroacetic acid → HCID 57562516, compound

HRID 1725629Notes

Reaction equation

HRID 1725629 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][N:12]2[C:18](=[O:19])[C@H:17]([NH:20]C(=O)OC(C)(C)C)[CH2:16][S:15](=[O:29])(=[O:28])[C@@H:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:13]2)[CH2:10][CH2:9]1>ClCCl>[NH2:20][C@@H:17]1[CH2:16][S:15](=[O:29])(=[O:28])[C@@H:14]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:13][N:12]([CH2:11][CH:8]2[CH2:10][CH2:9]2)[C:18]1=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86616778HCID 86616778, compound

Product 1

HCID 57562516HCID 57562516, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.0 mL) was added to a solution of tert-butyl (2S,6S)-4-(cyclopropylmethyl)-1,1-dioxido-5-oxo-2-phenyl-1,4-thiazepan-6-ylcarbamate (63 mg, 0.167 mmol) in dichloromethane (5 mL). After 1 h, the mixture was concentrated and aqueous saturated sodium bicarbonate was added. The mixture was extracted with dichloromethane (2×), and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to give the crude product (50 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. additionaqueous saturated sodium bicarbonate was added
  3. extractionThe mixture was extracted with dichloromethane (2×)
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-58176d695f134df8aa00a4a4eb0eafeb
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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