Ethyl Acetate → HCID 69584937, compound

HRID 1582363Notes

Reaction equation

HRID 1582363 reaction equation
[OH:1][C@@H:2]([CH2:33][OH:34])[C:3]([N:5]1[CH2:10][CH2:9][C:8]([C:11]2[C:16]([F:17])=[CH:15][C:14]([N:18]3[CH2:22][C@H:21]([CH2:23]NC4C=NC=CN=4)[O:20][C:19]3=[O:31])=[CH:13][C:12]=2[F:32])=[CH:7][CH2:6]1)=[O:4].[C:35]([O:39][C:40]([NH:42][C:43]1[N:48]=[CH:47][CH:46]=[CH:45][N:44]=1)=[O:41])([CH3:38])([CH3:37])[CH3:36].N1[CH:54]=[CH:53]N=CC=1.[C:55](OCC)(=O)C>ClCCl>[CH3:55][C:53]1([CH3:54])[O:1][C@H:2]([C:3]([N:5]2[CH2:10][CH2:9][C:8]([C:11]3[C:12]([F:32])=[CH:13][C:14]([N:18]4[CH2:22][C@H:21]([CH2:23][N:42]([C:43]5[N:44]=[CH:45][CH:46]=[CH:47][N:48]=5)[C:40]([O:39][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:41])[O:20][C:19]4=[O:31])=[CH:15][C:16]=3[F:17])=[CH:7][CH2:6]2)=[O:4])[CH2:33][O:34]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9261PyrazineHCID 10976384tert-Butyl pyrimidin-2-ylcarbamateHCID 207256613-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-pyrazin-2-ylaminomethyloxazolidin-2-one

Product 1

HCID 69584937HCID 69584937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Essentially the technique for the appropriate intermediate of Example 22 was used, but substituting 2-(t-butoxycarbonylamino)pyrimidine (293 mg, 1.5 mM) for the pyrazine analogue. To complete the reaction, heating at 80° for 1 hour was necessary, and the chromatography was carried out with a gradient from 0% to 50% ethyl acetate in dichloromethane containing 2% triethylamine. Relevant fractions were combined to give the desired product (427 mg). NMR (DMSO-d6) δ: 1.32 (s, 3H); 1.34 (s, 3H); 1.41 (s, 9H); 2.30 (br, 1H); 2.38 (br, 1H); 3.67 (t, 1H); 3.75 (m, 1H); 3.87 (dd, 1H); 4.00-4.33 (overlapping m, 7H); 4.90 (dd, 1H); 5.01 (m, 1H); 5.87 (s, 1H); 7.27 (t, 1H); 7.31 (d, 2H); 8.73 (d, 2H). MS (ESP): 616 (MH+) for C30H35F2N5O7

Workup

  1. customthe reaction
  2. temperatureheating at 80° for 1 hour

Sources & evidence

ORD record
ord-cae631f3640444859527e0797a7fa7b4
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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