4-Methylmorpholine → HCID 88629761, compound

HRID 2291384Notes

Reaction equation

HRID 2291384 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11](/[C:13](=[N:17]/[O:18][CH3:19])/[C:14]([OH:16])=O)[N:12]=1)=[O:6])[CH:2]=[CH2:3].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[C:39]([C:43]1[CH2:50][N:49]2[N:45]([C:46](=[O:52])[CH:47]([NH2:51])[CH2:48]2)[C:44]=1[C:53]([O:55][CH2:56][CH:57]=[CH2:58])=[O:54])(=[O:42])[CH2:40][CH3:41]>C(Cl)Cl.C(OCC)(=O)C>[C:39]([C:43]1[CH2:50][N:49]2[N:45]([C:46](=[O:52])[CH:47]([NH:51][C:14](=[O:16])/[C:13](/[C:11]3[N:12]=[C:8]([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[S:9][CH:10]=3)=[N:17]\[O:18][CH3:19])[CH2:48]2)[C:44]=1[C:53]([O:55][CH2:56][CH:57]=[CH2:58])=[O:54])(=[O:42])[CH2:40][CH3:41]

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 14544664HCID 14544664, compoundHCID 21279960HCID 21279960, compound

Product 1

HCID 88629761HCID 88629761, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 2-[2-(allyloxycarbonylamino)thiazol-4-yl]-2-(Z)-methoxyiminoacetic acid (248 mg, 0.87 mmol) was suspended in methylene chloride (5 ml) and the suspension was cooled to 0° C. 2-Chloro-4,6-dimethoxy-1,3,5-triazine (153 mg, 0.87 mmol) then N-methylmorpholine (0.095 ml, 0.87 mmol) were added and the resultant solution was stirred at 0° C. for 30 minutes. A methylene chloride solution (10 ml) of allyl 3-(propionyl)-7-(R,S)-amino-8-oxo-1,5-diazabicyclo[3.3.0]octa-2-ene-2-carboxylate hydrochloride (0.87 mmol) was added followed by the addition of N-methylmorpholine (0.095 ml, 0.87 mmol). The solution was allowed to warm gradually to room temperature over 1.5 hours and then the methylene chloride was removed in vacuo. The resultant residue was flash chromatographed on silica gel eluted with 10% hexane:ethyl acetate to give 270 mg, 57% yield of allyl 3-(propionyl)-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: n.m.r. (90 MHz, CDCl3): δ 1.11 (t, 3, J=7.2), 2.39-2.79 (m, 2), 3.09 (dd, 1, J=9 and 11.7), 3.95 (s, 3), 3.80-4.24 (m, 3), 4.42 (1/2ABq, 1, J=12.5), 4.60-4.96 (m, 4), 5.16-5.68 (m, 4), 5.72-6.22 (m, 2), 7.09 (s, 1), 8.28 (br.d, 1, J=7.2), 9.55 (br.s, 1); i.r. (CHCl3): 3230, 1733, 1679, 1554, 1423, 1377, 1353, 1044 cm-1 ; u.v. (EtOH): λhd max=208 (ε=21522), 228 (ε=22084), 261 (ε=13612), 365 (ε=8122); f.d.m.s. (m/e): M+ +1=547; m.p. 183°-186° C.

Workup

  1. temperatureto warm gradually to room temperature over 1.5 hours
  2. customthe methylene chloride was removed in vacuo
  3. customchromatographed on silica gel
  4. washeluted with 10% hexane

Sources & evidence

ORD record
ord-78a489ea62424660a4677f1a8b5abdf4
Source dataset
uspto-grants-1989_01
Patent number
US04795815

Reaction notes

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