Triethylamine → Trifluoromethanesulfonate

HRID 77322

Reaction equation

[C:1]([O:5][C:6](=[O:31])[C@@H:7]([CH:28]([CH3:30])[CH3:29])[N:8]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:39]([O:46]S(C(F)(F)F)(=O)=O)([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40]>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:31])[C@@H:7]([CH:28]([CH3:30])[CH3:29])[N:8]([CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][S:39]([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:3])([CH3:4])[CH3:2].[O-:46][S:39]([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (0.18 g, 0.35 mmol) in dichloromethane (10 mL) at 0° C. is added triethylamine (0.099 mL, 0.71 mmol), triflic anhydride (0.089 mL, 0.53 mmol), and 4-dimethylaminopyridine (0.004 g, 0.035 mmol). The reaction is stirred at 0° C. for 1 hour. The solvents are removed in vacuo, and the residue is purified by column chromatography (6% hexanes-ethyl acetate) to afford the title compound (a triflate) as a yellow solid (0.14 g, 68% yield).

Workup

customThe solvents are removed in vacuo
customthe residue is purified by column chromatography (6% hexanes-ethyl acetate)

Sources & evidence

ORD record: ord-ff2caca0eef64b8a8e81656a051c760e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841291B2

Linked notes

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