Trifluoroacetic acid → HCID 86587117, compound

HRID 1976426Notes

Reaction equation

HRID 1976426 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2([C:24]([O-:26])=[O:25])[NH:21][CH2:20][CH2:19][CH2:18][S:17][C:16]2([CH3:23])[CH3:22])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2([C:24]([OH:26])=[O:25])[NH:21][CH2:20][CH2:19][CH2:18][S:17][C:16]2([CH3:22])[CH3:23])(=[O:13])=[O:14])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86587118HCID 86587118, compound

Product 1

HCID 86587117HCID 86587117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (3S)4-({[4-(2-butynyloxy)phenyl]sulfonyl}-2,2-dimethyl-1,4-thiazepane-3-carboxylate (220 mg, 0.49 mmol) in methylene chloride (4 mL) was added trifluoroacetic acid (1.5 mL) and the mixture was stirred for 2 h at room temperature. The solvent was removed in vacuo. Traces of trifluoroacetic acid was removed by adding toluene (1 mL) and removing the solvent to obtain 170 mg (88%) of (3S)-4-({[4-(2-butynyloxy)phenyl]sulfonyl}-2,2-dimethyl-1,4-thiazepane-3-carboxylic acid; 1H NMR (300 MHz, CDCl3) δ 1.42 (s, 3H), 1.60 (s, 3H), 1.85 (m, 3H), 1.91 (m, 1H), 2.17 (m, 1H), 2.67 (m, 1H), 2.82 (m, 1H), 3.54 (m, 1H), 3.82 (m, 1H), 4.59 (s, 1H), 4.68 (m, 2H), 7.0 (d, 2H, J=8.7 Hz), 7.75 (d, 2H, J=8.7 Hz); HRMS (C18H23NO5S2)(M+);

Workup

  1. customThe solvent was removed in vacuo
  2. customTraces of trifluoroacetic acid was removed
  3. additionby adding toluene (1 mL)
  4. customremoving the solvent

Sources & evidence

ORD record
ord-985659e95c0b41b38b4ce81ba3b05c76
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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