Hydrochloric Acid → HCID 86592509, compound

HRID 1374392Notes

Reaction equation

HRID 1374392 reaction equation
[H-].[Na+].[OH:3][CH2:4][C@@H:5]1[CH2:10][C:9]([C:11]2[N:12]=[C:13]([SH:16])[S:14][CH:15]=2)=[CH:8][CH2:7][N:6]1[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18].O(P(OC1C=CC=CC=1)O[C:32]1[C@H:38]([CH3:39])[C@H:37]2[N:34]([C:35](=[O:47])[C@@H:36]2[C@H:40]([O:42][Si](C)(C)C)[CH3:41])[C:33]=1[C:48]([O:50][CH2:51][CH:52]=[CH2:53])=[O:49])C1C=CC=CC=1.C(#N)C.Cl>C1COCC1.CN(C=O)C>[CH2:20]([O:19][C:17]([N:6]1[CH2:7][CH:8]=[C:9]([C:11]2[N:12]=[C:13]([S:16][C:32]3[C@H:38]([CH3:39])[C@H:37]4[N:34]([C:35](=[O:47])[C@@H:36]4[C@H:40]([OH:42])[CH3:41])[C:33]=3[C:48]([O:50][CH2:51][CH:52]=[CH2:53])=[O:49])[S:14][CH:15]=2)[CH2:10][C@H:5]1[CH2:4][OH:3])=[O:18])[CH:21]=[CH2:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 86592502HCID 86592502, compoundHCID 178459663HCID 178459663, compound

Product 1

HCID 86592509HCID 86592509, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60 w/w %, 13.3 mg, 0.33 mmol) was added at 0–5° C. to a solution of allyl (2S)-2-(hydroxymethyl)-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (purity 70%, 139 mg, 0.33 mmol) in a mixture of THF (11.0 ml) and DMF(0.5 ml) and the mixture was stirred for 10 minutes. To the reaction solution was added at 0° C. a solution of allyl (4R,5R,6S)-3-[(diphenoxyphosphino)oxy]-4-methyl-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate in acetonitrile (30%, 1.27 g, 0.67 mmol) and the solution was allowed to stand in a refrigerator for 16 hours. To the reaction solution was added ice water and the solution was adjusted to pH 3 at 0–5° C. with 1N hydrochloric acid. After the mixture was stirred for 30 minutes, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the solvent in vacuo, the residue was purified with thin layer chromatography (10% methanol in chloroform) to give allyl (4R,5S,6S)-3-({4-[(2S)-1-[(allyloxy)carbonyl]-2-(hydroxymethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1,3-thiazol-2-yl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (87 mg, 46%).

Workup

  1. waitto stand in a refrigerator for 16 hours
  2. stirringAfter the mixture was stirred for 30 minutes
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal of the solvent in vacuo
  7. customthe residue was purified with thin layer chromatography (10% methanol in chloroform)

Sources & evidence

ORD record
ord-65c30055ba8e47a6801c6a46a008d847
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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