4-Methylmorpholine → HCID 67548010, compound

HRID 1985789Notes

Reaction equation

HRID 1985789 reaction equation
N[C@@H](C[S:6][CH2:7][CH:8]1[CH2:10][CH2:9]1)CO.CN1CCOCC1.FC(F)(F)C(OS(C(F)(F)F)(=O)=O)C1C=CC=CC=1.C1C(C[C@:41]([NH:46][CH:47]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:48]([F:51])([F:50])[F:49])([CH3:45])[CH:42](S)[OH:43])C1>C1COCC1>[CH2:9]1[CH:8]([CH2:7][S:6][C@:41]([NH:46][CH:47]([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:48]([F:49])([F:50])[F:51])([CH3:45])[CH2:42][OH:43])[CH2:10]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 11666699HCID 11666699, compoundHCID 58515553HCID 58515553, compoundHCID 86600267HCID 86600267, compound

Product 1

HCID 67548010HCID 67548010, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2(R)-amino-3-cyclopropylmethylsulfanylpropan-1-ol (80.5 mg, 0.5 mmol) in anhydrous THF (3 mL) were added activated 4A molecular sieves (250 mg) and N-methylmorpholine (51 mg, 0.5 mmol). After stirring for 10 min, trifluoromethanesulfonic acid 2,2,2-trifluoro-1-phenylethyl ester (190.5 mg, 0.5 mmol) was added and the reaction was stirred at room temperature for 2 days. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by flash column chromatography to afford the desired mixture of diastereomers of 2(R)-3-cyclopropylmethyl-sulfanyl-2-(2,2,2-trifluoro-1(RS)-phenylethylamino)-propan-1-ol. LC-MS: 318.3(M−1), 320.8(M+1).

Workup

  1. stirringthe reaction was stirred at room temperature for 2 days
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by flash column chromatography
  5. customto afford the desired

Sources & evidence

ORD record
ord-b94640bef0354184bd9ff3cce9c3df08
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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