Triethylamine → HCID 10288107, compound

HRID 1816444Notes

Reaction equation

HRID 1816444 reaction equation
Cl.[NH2:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[C:14]([F:16])[C:13]([CH:17]3[CH:22]=[CH:21][S:20](=[O:24])(=[O:23])[CH2:19][CH2:18]3)=[C:12]([F:25])[CH:11]=2)[CH2:5]1.[F:26][CH:27]([F:33])[C:28](OCC)=[O:29].C(N(CC)CC)C>CO>[O:24]=[S:20]1(=[O:23])[CH:19]=[CH:18][CH:17]([C:13]2[C:14]([F:16])=[CH:15][C:10]([N:6]3[CH2:5][C@H:4]([CH2:3][NH:2][C:28](=[O:29])[CH:27]([F:33])[F:26])[O:8][C:7]3=[O:9])=[CH:11][C:12]=2[F:25])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9961Ethyl difluoroacetateHCID 69371271HCID 69371271, compound

Product 1

HCID 10288107HCID 10288107, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5S)-5-(aminomethyl)-3-[4-(1,1-dioxido-3,4-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-1,3-oxazolidin-2-one monohydrochloride from Step 1 (0.400 g, 1.02 mmol), ethyl difluoroacetate (0.633 g, 5.1 mmol), and triethylamine (0.284 ml, 2.04 mmol) in methanol (8 ml) were stirred at room temperature overnight. The reaction mixture was evaporated to dryness and the residue purified by PTLC (10% methanol/dichloromethane) to give white solid (0.36 g, 80%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue purified by PTLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-62e359a861024ebcac5aaf521b057e6a
Source dataset
uspto-grants-2005_04
Patent number
US06884813B2

Reaction notes

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