Ethyl dichloroacetate → HCID 117662144, compound

HRID 1484417Notes

Reaction equation

HRID 1484417 reaction equation
OC(C(F)(F)F)=O.[NH2:8][C@H:9]([CH2:25][F:26])[C@@H:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:24])(=[N:20][C:21](=[O:23])[NH2:22])=[O:19])=[CH:14][CH:13]=1)[OH:11].C([O:29][C:30](=O)[CH:31]([Cl:33])[Cl:32])C>CO>[C:21]([N:20]=[S:18]([C:15]1[CH:14]=[CH:13][C:12]([C@@H:10]([OH:11])[C@H:9]([NH:8][C:30](=[O:29])[CH:31]([Cl:33])[Cl:32])[CH2:25][F:26])=[CH:17][CH:16]=1)([CH3:24])=[O:19])(=[O:23])[NH2:22]

Participants

4

Reactant 2

HCID 10808Ethyl dichloroacetateHCID 131736730HCID 131736730, compound

Product 1

HCID 117662144HCID 117662144, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1R,2S)-2-Amino-3-fluoro-1-(4-(N-carbamoyl-S-methylsulfonimidoyl)phenyl)-propan-1-ol TFA salt (250 mg, 0.865 mmol) in Methanol (5 mL) is added TEA (0.175 mL, 1.73 mmol) followed by addition of ethyldichloroacetate (128.72 mL, 1.038 mmol) at room temperature. The resulting reaction mixture is stirred at room temperature for 16 h. Solvent is evaporated in vacuo and obtained crude is purified by combi-flash chromatography using 6% MeOH in DCM as an eluent to give 200 mg of title compound as off white solid. 1H-NMR (400 MHz, DMSO): δ 2.99 (s, 3H), 4.25-4.32 (m, 1.5H), 4.40-4.44 (m, 0.5H), 4.56-4.59 (m, 0.5H), 4.67-4.71 (m, 0.5H), 4.97 (bs, 1H), 6.05 (bs, 1H), 6.18 (m, 1H), 6.46-6.48 (m, 1H), 7.61 (d, J=7.52 Hz, 2H), 7.86 (d, J=8 Hz, 2H), 8.63-8.67 (m, 2H). LC-MS (m/z): M+H=399.8.

Workup

  1. customThe resulting reaction mixture
  2. customSolvent is evaporated in vacuo
  3. customobtained crude
  4. customis purified by combi-flash chromatography

Sources & evidence

ORD record
ord-f95f0ee600294dd08cfe366f77a05297
Source dataset
uspto-grants-2016_08
Patent number
US09422236B2

Reaction notes

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