Hydrochloric Acid → HCID 14973524, compound

HRID 2291382Notes

Reaction equation

HRID 2291382 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH2:18][N:17]2[N:13]([C:14](=[O:38])[CH:15]([NH:19][C:20](=[O:37])/[C:21](/[C:25]3[N:26]=[C:27]([NH:30]C(OCC=C)=O)[S:28][CH:29]=3)=[N:22]\[O:23][CH3:24])[CH2:16]2)[C:12]=1[C:39]([O:41]CC=C)=[O:40])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([SnH](CCCC)CCCC)CCC.Cl>C(#N)C.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)=O>[CH2:1]([O:8][C:9]([C:11]1[CH2:18][N:17]2[N:13]([C:14](=[O:38])[CH:15]([NH:19][C:20](=[O:37])/[C:21](/[C:25]3[N:26]=[C:27]([NH2:30])[S:28][CH:29]=3)=[N:22]\[O:23][CH3:24])[CH2:16]2)[C:12]=1[C:39]([OH:41])=[O:40])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 5948TributylstannaneHCID 11776TriphenylphosphineHCID 88630118HCID 88630118, compound

Product 1

HCID 14973524HCID 14973524, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, allyl 3-(benzyloxycarbonyl)-7-(R,S)-[2-(2-(allyloxycarbonylamino)thiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-8-oxo-1,5-diazabicyclo[3,3.0]octa-2-ene-2-carboxylate (340 mg, 0.54 mmol) was suspended in a mixture of acetonitrile (10 ml) and diethyl ether (5 ml) then palladium(II) acetate (6.1 mg, 0.027 mmol,) and triphenylphosphine (56.7 mg, 0.216 mmol,) were added. Acetone (20 ml) was added and the resultant solution was stirred for 30 minutes at room temperature then cooled to 0° C. Tri(n-butyl)tin hydride (0.3 ml, 1.1 mmol) was added and the solution was stirred for 1.5 hours at room temperature. 12N hydrochloric acid (0.09 ml, 1.1 mmol) was added and the solution was concentrated in vacuo. The resultant residue was dissolved in methylene chloride, diethyl ether was added to effect precipitation and the precipitate was collected by filtration to give 3-(benzyloxycarbonyl)-7-(R,S)-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-8-oxo-1,5 -diazabicyclo[3.3.0]octa-2-ene-2-carboxylic acid: n.m.r. (90 MHz, DMSO-d6): δ 2.60-4.14 (m, 5), 3.76 (s, 3), 4.64-5.20 (m, 2), 5.04 (s, 2), 7.12 (br. s, 2), 7.24 (br. s, 5), 9.01 (br. d, 1, J=7); i.r. (KBr): 3417, 1696, 1662, 1617, 1521, 1442, 1396, 1380, 1331, 1272 cm-1 ; u.v. (EtOH); λmax =231 (ε=15547), 329 (ε=11296); m.p. d>160° C.°, f.a.b.m.s. (m/e) M+1=501.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in methylene chloride
  3. additiondiethyl ether was added to effect precipitation
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c862c8665f644b68a3450eb8b262b308
Source dataset
uspto-grants-1989_01
Patent number
US04795815

Reaction notes

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