Trifluoroacetic acid → HCID 16075330, compound

HRID 1795125Notes

Reaction equation

HRID 1795125 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]2[CH2:21][CH:20]2[NH:22][C:23](OC(C)(C)C)=[O:24])(=[O:11])=[O:10])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.C(N(CC)CC)C.[CH2:46]1[O:50][C:49]2[CH:51]=[C:52]([CH2:55]C(O)=O)[CH:53]=[CH:54][C:48]=2[O:47]1.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C@H:19]2[CH2:21][C@@H:20]2[NH:22][C:23](=[O:24])[CH2:55][C:52]2[CH:53]=[CH:54][C:48]3[O:47][CH2:46][O:50][C:49]=3[CH:51]=2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 22185691HCID 22185691, compound

Product 1

HCID 16075330HCID 16075330, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 2-{2-[(tert-butoxycarbonyl)amino]cyclopropyl}phenyl 4-(trifluoromethyl)benzenesulfonate (0.09 g, 0.2 mmol) in methylene chloride (1 mL) is treated with trifluoroacetic acid (0.1 mL) at room temperature for 2 hours. The reaction is evaporated in vacuo to a white solid. The solid is treated with N,N-dimethylacetamide (0.3 mL), and triethylamine (27 □L, 0.2 mmol). A mixture of 3,4-(methylenedioxy)phenylacetic acid (39 mg, 0.22 mmol), 4-dimethylaminopyridine (27 mg, 0.22 mmol), and N,N-dimethylacetamide (0.1 mL) is added to the reaction, followed by the addition of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (42 mg, 0.22 mmol). The reaction is stirred at room temperature overnight. After work-up with ethyl acetate-hexane-water, the dried, evaporated residue is purified on silica gel in ethyl acetate-methylene chloride mixtures. The product, 2-((1R,2S)-2-{[2-(1,3-benzodioxol-5-yl)acetyl]amino}cyclopropyl)phenyl 4-(trifluoromethyl)-benzenesulfonate, is recrystallized from methanol-water. A yield of 80% is obtained. 1H NMR (400 MHz, CDCl3) d 1.15 (m, 1H); 1.25 (m, 1H); 2.07 (m, 1H); 2.80 (m, 1H); 3.50 (s, 2H); 5.97 (m, 3H); 6.78 (m, 4H); 7.05 (m, 1H); 7.13 (m, 1H); 7.21 (m, 1H); 7.85 (m, 2H); 8.02 (m, 2H). ESI+ for C25H20F3NO6S m/z=520 (M+H)+.

Workup

  1. customThe reaction is evaporated in vacuo to a white solid
  2. additionis added to the reaction
  3. customAfter work-up with ethyl acetate-hexane-water, the dried, evaporated residue
  4. customis purified on silica gel in ethyl acetate-methylene chloride mixtures
  5. customThe product, 2-((1R,2S)-2-{[2-(1,3-benzodioxol-5-yl)acetyl]amino}cyclopropyl)phenyl 4-(trifluoromethyl)-benzenesulfonate, is recrystallized from methanol-water
  6. customA yield of 80% is obtained

Sources & evidence

ORD record
ord-84814a52ec7745b58a105ace0c303fd7
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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