Ethyl Acetate → HCID 86757661, compound

HRID 2269354Notes

Reaction equation

HRID 2269354 reaction equation
[CH:1]([N:3]([O:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][O:36]1)[C@@H:4]([CH3:33])[C@@H:5]([CH2:20][CH:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)[C:6](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:7])=[O:2].[S:41]1[CH:45]=[CH:44][N:43]=[C:42]1[NH:46][C:47](=[O:54])[C@@H:48]([NH2:53])[C:49]([CH3:52])([CH3:51])[CH3:50].C1C=CC2N(O)N=NC=2C=1.CCOC(C)=O>CN(C=O)C>[CH3:52][C:49]([CH3:51])([CH3:50])[C@H:48]([NH:53][C:6](=[O:7])[C@H:5]([CH2:20][CH:21]1[CH2:22][CH2:23][CH:24]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:25][CH2:26]1)[C@@H:4]([N:3]([CH:1]=[O:2])[O:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][O:36]1)[CH3:33])[C:47](=[O:54])[NH:46][C:42]1[S:41][CH:45]=[CH:44][N:43]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 21310047HCID 21310047, compoundHCID 57005544HCID 57005544, compound

Product 1

HCID 86757661HCID 86757661, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
41 °C

Procedure

A mixture of pentafluorophenyl (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoate (0.25 g, 0.44 mmol), (2S)-2-amino-3,3-dimethylbutanoic acid 1,3-thiazol-2-ylamide (0.10 g, 0.49 mmol), HOBt (6.1 mg, 0.040 mmol) and TEA (0.07 g, 0.67 mmol) in DMF (3 mL) is heated at 41° C. for 18 h. The reaction mixture is poured into a mixture of hexanes (100 mL) and EtOAc (100 mL) and the resulting mixture is washed with water, 1 M aqueous sodium carbonate and water. The organic phase is dried (sodium sulfate) and concentrated in vacuo and the residue is purified by column chromatography on silica gel with EtOAc-hexanes (1:1) as eluent to give 0.12 g (46%) of (2R,3S)-3-(formyltetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoic acid [(1S)-2,2-dimethyl-1-(1,3-thiazol-2-ylcarbamoyl)-1-propyl]amide as a white solid.

Workup

  1. washthe resulting mixture is washed with water, 1 M aqueous sodium carbonate and water
  2. dry with materialThe organic phase is dried (sodium sulfate)
  3. concentrationconcentrated in vacuo
  4. customthe residue is purified by column chromatography on silica gel with EtOAc-hexanes (1:1) as eluent

Sources & evidence

ORD record
ord-6912d40bbf4440598c34d0cb724ef4e1
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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