Potassium azide → HCID 131715738, compound

HRID 2231691Notes

Reaction equation

HRID 2231691 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.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

6

Reactant 3

HCID 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 micro mol) 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 micro mol) 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 etherdichloromethane 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-70da303c65eb42e998a008e51bae94cb
Source dataset
uspto-grants-1988_11
Patent number
US04783453

Reaction notes

Loading…