2,2,2-Trifluoroethylamine hydrochloride → HCID 86593165, compound

HRID 2212248Notes

Reaction equation

HRID 2212248 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].C(N(C(C)C)CC)(C)C.Cl.[F:23][C:24]([F:28])([F:27])[CH2:25][NH2:26].[NH2:29][CH:30]([CH2:48][S:49]([CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)(=[O:51])=[O:50])[C:31]([NH:33][CH:34]([CH:37]([C:39]1[O:40][C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=1)[OH:38])[CH2:35][CH3:36])=[O:32]>C(Cl)Cl.CCOC(C)=O>[O:40]1[C:41]2[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=2[N:43]=[C:39]1[CH:37]([OH:38])[CH:34]([NH:33][C:31](=[O:32])[CH:30]([NH:29][C:1]([NH:26][CH2:25][C:24]([F:28])([F:27])[F:23])=[S:2])[CH2:48][S:49]([CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)(=[O:50])=[O:51])[CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 69616497HCID 69616497, compound

Product 1

HCID 86593165HCID 86593165, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,1′-Thiocarbonyldiimidazole (0.980 g, 5.50 mmol, 1.2 equiv.) was dissolved in CH2Cl2 (200 mL), followed by addition of diisopropylethylamine (3.2 mL), and trifluoroethylamine hydrochloride (0.620 g, 4.58 mmol, 1.0 equiv.). The solution was stirred for 1 h at ambient temp, then 2-amino-N-[1-(benzoxazol-2-ylhydroxymethyl)-propyl]-3-phenylmethanesulfonylpropionamide was added in one portion. After stirring overnight, the reaction mixture was diluted with EtOAc (150 mL), washed with saturated bicarb, brine, dried over MgSO4. Purification with flash chromatography (50% ETOAc/hexanes as eluent) afforded N-[1-(benzoxazol-2-ylhydroxymethyl)-propyl]-3-phenylmethanesulfonyl-2-[3-(2,2,2-trifluoroethyl)thioureido]propionamide (0.720 g) as a mixture of diasteomers.

Workup

  1. stirringAfter stirring overnight
  2. washwashed with saturated bicarb, brine
  3. dry with materialdried over MgSO4
  4. customPurification with flash chromatography (50% ETOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-de6e5ea6b7344be091cdaa068db9551c
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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