4-Cyclohexylphenol → HCID 59252509, compound

HRID 237834Notes

Reaction equation

HRID 237834 reaction equation
[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]([NH2:18])=[N:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1O[C@H]1CCl.C1(C2C=CC(O)=CC=2)CCCCC1.C([O:41][C:42](=O)[C:43]([S:46][CH3:47])=[CH:44]O)C>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]4=[N:18][C:42](=[O:41])[C:43]([S:46][CH3:47])=[CH:44][N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 143274-CyclohexylphenolHCID 2734062(-)-EpichlorohydrinHCID 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamineHCID 86640235HCID 86640235, compound

Product 1

HCID 59252509HCID 59252509, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.91 g, 3.34 mmol) (prepared in accordance with the procedures set forth in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 4-cyclohexylphenol) in toluene (50 mL) was added 3-hydroxy-2-methylsulfanyl-acrylic acid ethyl ester (1.08 g, 6.68 mmol) prepared in accordance with the procedures in Step 1 of Example 87 The reaction mixture was heated at 80° C. for 18 hours. The reaction mixture was concentrated and loaded onto a silica gel column and eluted with 0-5% 2-propanol/CH2Cl2 to afford 0.44 g of the title compound. [α]D25 +18.24 (c 0.537, CHCl3)

Workup

  1. customprepared in accordance with the procedures in Step 1 of Example 87 The reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. washeluted with 0-5% 2-propanol/CH2Cl2

Sources & evidence

ORD record
ord-4364537308ff47f299c2da9fb46e543f
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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