Malonic Acid → HCID 86734830, compound

HRID 1439506Notes

Reaction equation

HRID 1439506 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([C:22]([NH:35][CH:36]2[C:56](=[O:57])[N:38]3[CH:39]([C:44](=[N:46][CH2:47][C:48]4[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=4)[NH2:45])[C:40]([CH3:43])([CH3:42])[S:41][C@H:37]23)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:58](O)(=[O:63])[CH2:59][C:60](O)=[O:61]>CN(C)C=O.C(Cl)Cl>[C:29]1([C:22]([NH:35][CH:36]2[C:56](=[O:57])[N:38]3[CH:39]([C:44]4[N:46]([CH2:47][C:48]5[CH:49]=[CH:50][C:51]([O:54][CH3:55])=[CH:52][CH:53]=5)[C:58](=[O:63])[CH2:59][C:60](=[O:61])[N:45]=4)[C:40]([CH3:43])([CH3:42])[S:41][C@H:37]23)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 867Malonic AcidHCID 10868DicyclohexylcarbodiimideHCID 70637607HCID 70637607, compound

Product 1

HCID 86734830HCID 86734830, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 21.44 g. (104 mmoles) of N,N'-dicyclohexylcarbodiimide in 122 ml. of methylene chloride and 15 ml. dimethylformamide at -5° C., a solution of 29.9 g. (52 mmoles) of 6-(triphenylmethylamino)-2,2-dimethyl-3-[N'-(4-methoxybenzyl)amidino]penam and 5.41 g. (52 mmoles) of malonic acid in 122 ml. methylene chloride and 15 ml. dimethylformamide is added dropwise over 2 hours. The mixture is then stirred for 24 hours at 25° C. The N,N'-dicyclohexylurea precipitate (18.6 g., 79.8% of theory) is filtered off, and the filtrate washed with six 150 ml. portions of water. It is dried over anhydrous sodium sulfate and then rotoevaporated to yield the title compound in crude form as an orange foam (32.6 g.). The crude product is divided into two equal portions for silica gel chromatography (ethyl acetate elution) affording a total of 10.61 g. (31.6%) of the purified title compound. 1H-NMR (CDCl3) ppm (δ) 1.01 (3H, s, 2-CH3); 1.44 (3H, s, 2CH3); 3.80 (3H, s, --OCH3); 4.31-4.73 (3H, m; 3-, 5- and 6H); 5.25 (2H, s, --CH2 --); 4H, AB, Ha within a 7.18-7.68 multiplet, Hb centered at 6.91, J = 8 Hz, CH3O--C6-4H--); 7.18-7.68 (15H, m, C6-5H--).

Workup

  1. customat -5° C.
  2. filtrationThe N,N'-dicyclohexylurea precipitate (18.6 g., 79.8% of theory) is filtered off
  3. washthe filtrate washed with six 150 ml
  4. dry with materialIt is dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-60a8d9d9816d4208a604eb51733b1161
Source dataset
uspto-grants-1977_11
Patent number
US04060524

Reaction notes

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