Trifluoroacetic acid → HCID 57562521, compound

HRID 1725627Notes

Reaction equation

HRID 1725627 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][C@@H:14]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:13]2)[CH2:10][CH2:9]1>ClCCl>[NH2:20][C@@H:17]1[CH2:16][S:15][C@@H:14]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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 86616777HCID 86616777, compound

Product 1

HCID 57562521HCID 57562521, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.0 mL) was added to a solution of tert-butyl (2S,6S)-4-(cyclopropylmethyl)-5-oxo-2-phenyl-1,4-thiazepan-6-ylcarbamate (90 mg, 0.239 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 (57 mg). 1H NMR (500 MHz, CDCl3) □ 7.38-7.30 (m, 5H), 4.36-4.28 (m, 2H), 4.06 (d, J=9.3 Hz, 1H), 3.74 (dd, J=14.4, 1.5 Hz, 1H), 3.67 (dd, J=13.9, 7.3 Hz, 1H), 3.08 (dd, J=13.9, 6.6 Hz, 1H), 3.00 (dd, J=14.4, 9.8 Hz, 1H), 2.66 (dd, J=14.4, 1.9 Hz, 1H), 1.02-0.99 (m, 1H), 0.57-0.53 (m, 2H), 0.27-0.23 (m, 2H).

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-5d81ee4c91a64a118d427a262a30b7ff
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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