18-Crown-6 → HCID 131715738, compound

HRID 329663Notes

Reaction equation

HRID 329663 reaction equation
[N-:1]=[N+:2]=[N-:3].[K+].C1(C)C=CC(S(O[C:15]2[CH2:16][C@@H:17]3[CH2:31][C:30](=[O:32])[N:18]3[C:19]=2[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])(=O)=O)=CC=1.O1CCOCCOCCOCCOCCOCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>C(#N)C.ClCCl>[CH2:23]([O:22][C:20]([C:19]1[N:18]2[C:30](=[O:32])[CH2:31][C@H:17]2[CH2:16][C:15]=1[N:1]=[N+:2]=[N-:3])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 2855718-Crown-6HCID 10290740Potassium azideHCID 21584019Toluene ethylacetateHCID 131715739HCID 131715739, compound

Product 1

HCID 131715738HCID 131715738, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Potassium azide (11.6 mg, 143 micromol) was added to a stirred ambient temperature solution of benzyl 2-(p-toluenesulfonyloxy)-carbapen-2-em-3-carboxylate (20.0 mg, 48.4 micromol) prepared according to the analogous procedure described in U.S. Pat. No. 4,424,230, hereby incorporated by reference for this particular purpose, and 1,4,7,10,13,16-hexaoxacyclooctadecane (12.8 mg, 48.4 micromol) in anhydrous acetonitrile (1.0 ml) and dichloromethane (0.2 ml). After 1 hour the mixture was applied to two 20 cm×20 cm 250 micron silica gel preparative thin layer chromatography plates and developed with 3:2 (v/v) toluene-ethyl acetate. The band centered at Rf 0.6 was eluted with ethyl acetate and the elulate was evaporated under vacuum to provide 9.2 mg (67%) benzyl-2-azido-carbapen-2-em-3-carboxylate as a pale yellow glass. The glass was crystallized from 5:1 (v/v) diethyl ether-dichloromethane to provide pale yellow rosettes of needles, m.p. 84°-85° C. (dec); I.R. (neat film): 2110, 1785, 1710, 1605, 1285, 1210, 1190 cm-1 ; NMR (CDCl3): δ (del) 2.99 dd (J1 =3 Hz, J2 =16 Hz, 1H), 3.07 d (J=9 Hz, 2H), 3.52 dd (J1 =5 Hz, J2 =16 Hz, 1H), 4.25 m (1H), 5.30 d (J=8 Hz, 1H), 5.33 d (J=8 Hz, 1H), 7.37 m (5H); UV (CH2Cl2) λmax (ε): 310 (10,000) nm; MS (m/e): 256 (M+ --N2), 243, 228, 214, 178, 162, 160, 127, 120, 107.

Workup

  1. customprepared
  2. washwas eluted with ethyl acetate
  3. customthe elulate was evaporated under vacuum

Sources & evidence

ORD record
ord-1c594bfe125e4568b117c63661c62c89
Source dataset
uspto-grants-1990_01
Patent number
US04892869

Reaction notes

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