Water → HCID 59571717, compound

HRID 2194315Notes

Reaction equation

HRID 2194315 reaction equation
O1CCCC1.C([Li])CCC.[CH2:11]([C@H:18]1[CH2:22][O:21][C:20](=[O:23])[NH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:54]=[CH:55][C:56]=1[O:57][CH2:58][C:59]1[N:60]=[C:61]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[O:62][C:63]=1[CH3:64])[CH2:29][N:30]1[C:42]2[CH:41]=[CH:40][CH:39]=[C:38]([O:43][CH:44]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:45](Cl)=[O:46])[C:37]=2[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2.O>O1CCCC1>[CH3:64][C:63]1[O:62][C:61]([C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)=[N:60][C:59]=1[CH2:58][O:57][C:56]1[CH:55]=[CH:54][C:28]([CH2:29][N:30]2[C:42]3[CH:41]=[CH:40][CH:39]=[C:38]([O:43][CH:44]([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:45]([N:19]4[C@@H:18]([CH2:11][C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=5)[CH2:22][O:21][C:20]4=[O:23])=[O:46])[C:37]=3[C:36]3[C:31]2=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:27][C:26]=1[O:25][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 86647507HCID 86647507, compoundHCID 178420697HCID 178420697, compound

Product 1

HCID 59571717HCID 59571717, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

9.1 mL of 2.44M n-butyllithium tetrahydrofuran solution was added thereto dropwise to tetrahydrofuran (30 mL) solution of 3.92 g of (S)-4-benzyl-2-oxazolidinone at −50° C. The mixture was stirred at −50° C. for 1 hour. Thereafter, the solution of the previously prepared (±)-{9-[3-methoxy-4-(5-methyl-2-phenyl-oxazole-4-ylmethoxy)-benzyl]-9H-carbazole-4-yloxy}phenylacetyl chloride in tetrahydrofuran (30 mL) was added thereto dropwise at −50° C. After the dropwise addition thereto, the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, the prepared diastereomer mixture was purified by medium-pressure silica gel chromatography (ethyl acetate:n-hexane=5:1), and two types of the subject compound, 1.52 g of compound A (first fraction) and 1.2 g compound B (second fraction), were respectively prepared as pale brown powder.

Workup

  1. customat −50° C
  2. customdropwise at −50° C
  3. additionAfter the dropwise addition
  4. stirringthe mixture was stirred at room temperature overnight
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated in vacuo
  10. customthe prepared diastereomer mixture was purified by medium-pressure silica gel chromatography (ethyl acetate:n-hexane=5:1), and two types of the subject compound, 1.52 g of compound A (first fraction) and 1.2 g compound B (second fraction)
  11. customwere respectively prepared as pale brown powder

Sources & evidence

ORD record
ord-a57ec3459fe9435b8848e9cc0f563f15
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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