Trifluoroacetic acid → (1R,2S)-1-amino-2-ethenyl-N-{[-(methoxymethyl)cyclopropyl]sulfonyl}cyclopropanecarboxamide trifluoroacetate

HRID 522349Notes

Reaction equation

HRID 522349 reaction equation
[CH:1]([C@@H:3]1[CH2:5][C@:4]1([NH:18]C(=O)OC(C)(C)C)[C:6](=[O:17])[NH:7][S:8]([C:11]1([CH2:14][O:15][CH3:16])[CH2:13][CH2:12]1)(=[O:10])=[O:9])=[CH2:2].[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]>C(Cl)Cl>[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[NH2:18][C@:4]1([C:6]([NH:7][S:8]([C:11]2([CH2:14][O:15][CH3:16])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[O:17])[CH2:5][C@H:3]1[CH:1]=[CH2:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735528tert-butyl [(1R,2S)-2-ethenyl-1-({[1-(methoxymethyl)cyclopropyl]sulfonyl}carbamoyl)cyclopropyl]carbamate

Product 1

HCID 117598869(1R,2S)-1-amino-2-ethenyl-N-{[-(methoxymethyl)cyclopropyl]sulfonyl}cyclopropanecarboxamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of the product of Step 1 (120 mg) in DCM (1 mL) at 0° C. was added TFA (1 mL). The mixture was slowly warmed to room temperature and stirred for 3 hours. The solvent was removed in vacuo and the crude product was used in the next step. 1H NMR (400 MHz, CDCl3): δ (ppm) 5.82 (ddd, 1H), 5.44 (d, 1H), 5.43 (d, 1H), 3.67 (d, 1H), 3.63 (d, 1H), 3.35 (s, 3H), 2.64 (dt, 1H), 1.92 (dd, 1H), 1.83 (dd, 1H), 1.76-1.70 (m, 1H), 1.67-1.60 (m, 1H), 1.14-1.02 (m, 2H).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3ec1e32d4546440891442a217a74ede0
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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