Diisopropylethylamine → HCID 67908626, compound

HRID 467364Notes

Reaction equation

HRID 467364 reaction equation
C(N(CC)[CH:5]([CH3:7])[CH3:6])(C)C.[C:10]1([CH:16]([O:23][C:24]([C:26]2[N:31]3[C:32](=[O:44])[C@@H:33]([NH:34][C:35](=[O:43])[CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C@H:30]3[S:29][CH2:28][C:27]=2[SH:45])=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1>[O:25]=[C:24]1[CH:7]=[C:5]([CH2:6][S:45][C:27]2[CH2:28][S:29][C@@H:30]3[C@H:33]([NH:34][C:35](=[O:43])[CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:32](=[O:44])[N:31]3[C:26]=2[C:24]([O:23][CH:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:25])[CH2:16][O:23]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 88501947HCID 88501947, compound

Product 1

HCID 67908626HCID 67908626, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-Diisopropylethylamine (0.15 ml) was added to a stirred solution of diphenylmethyl-3-mercapto-7β-phenylacetamidoceph-3-em-4-carboxylate (500 mg) and 4-bromomethyl-2(5H)-furanone1 (200 mg) in tetrahydrofuran (10 ml). After stirring at room temperature for 90 mins. the mixture was partitioned between ethyl acetate and aqueous citric acid solution. The organic phase was separated and washed three times with water, then brine, dried over magnesium sulphate and evaporated. The title compound (474 mg) was isolated by column chromatography of the residue using gradient elution (Kieselgel 1:1 ethyl acetate:hexane going to neat ethyl acetate), m.p. 172°-176° C. from ethyl acetate/hexane. (Found: C, 64.24; H, 4.69; N, 4.51; S, 10.48; C33H28N2O6S2 requires; C, 64.69; H, 4.61; N, 4.57; S, 10.47); υmax (CHCl3) 3400, 1785, 1750, 1680 cm-1. δH (CDC13) 3.23 (1H, d, J 17.0Hz), 3.38 (1H, d, J 17.1Hz), 3.41 (H, d, J 15.2Hz), 3.53 (1H, d, J 15.1Hz), 3.66 (2H, s), 4.62 (2H, s), 4.98 (1H, d, J 4.6Hz), 5.76 (1H, dd, J 4.6 and 8.8Hz), 5.89 (1H, s), 6.56 (1H, d, J 8.8Hz) 6.91 (1H, s) 7.2-7.4 (15H, m).

Workup

  1. customthe mixture was partitioned between ethyl acetate and aqueous citric acid solution
  2. customThe organic phase was separated
  3. washwashed three times with water
  4. dry with materialbrine, dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-227acd74c0b74c178dbcdec5ecfce5c7
Source dataset
uspto-grants-1992_10
Patent number
US05158946

Reaction notes

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