Trifluoroacetic acid → HCID 86587119, compound

HRID 2414595Notes

Reaction equation

HRID 2414595 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH:15]2[CH:21]([C:22]([O-:24])=[O:23])[NH:20][CH2:19][CH2:18][CH2:17][S:16]2)(=[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]([CH:15]2[CH:21]([C:22]([OH:24])=[O:23])[NH:20][CH2:19][CH2:18][CH2:17][S:16]2)(=[O:13])=[O:14])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86587120HCID 86587120, compound

Product 1

HCID 86587119HCID 86587119, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Step 3 of Example 173, tert-butyl (3S)-4-({[4-(2-butynyloxy)phenyl]sulfonyl}-1,4-thiazepane-3-carboxylate (800 mg, 1.88 mmol), trifluoroacetic acid (6 mL) in methylene chloride (15 mL) provide 650 mg (94%) of (3S)-4-({[4-(2-butynyloxy)phenyl]sulfonyl}-1,4-thiazepane-3-carboxylic acid; 1H NMR (300 MHz, acetone-d6): δ1.74 (m, 3H), 1.90 (m, 2H), 2.59 (m, 2H), 2.90 (m, 1H), 3.18 (m, 1H), 3.26 (m, 1H), 3.70 (m, 1H), 4.70 (m, 3H), 7.03 (d, 2H, J=8.7 Hz), 7.77 (d, 2H, J=8.7 Hz); HRMS (C16H19NO5S2)(M+H); calcd. 370.0777, found 370.0765.

Sources & evidence

ORD record
ord-19ecb70869b84604964582eaf4f2c98b
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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