Oxalic Acid → HCID 77750336, compound

HRID 1069035Notes

Reaction equation

HRID 1069035 reaction equation
CC1(C)[O:6][CH:5]2[CH:7]([N:12]3[C:16]4[N:17]=[C:18]([S:31][CH2:32][CH2:33][CH3:34])[N:19]=[C:20]([NH:21][CH:22]5[CH2:24][CH:23]5[C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[C:15]=4[N:14]=[N:13]3)[CH2:8][CH:9](CO)[CH:4]2[O:3]1.F[C:37](F)(F)[C:38]([OH:40])=O.[CH:43]1(N=C=NC2CCCCC2)CCCCC1.COC(=O)C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C(O)=O>CS(C)=O.C(OCC)(=O)C.N1C=CC=CC=1>[OH:40][CH2:38][CH:37]=[CH:43][CH:9]1[CH2:8][CH:7]([N:12]2[C:16]3[N:17]=[C:18]([S:31][CH2:32][CH2:33][CH3:34])[N:19]=[C:20]([NH:21][CH:22]4[CH2:24][CH:23]4[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:15]=3[N:14]=[N:13]2)[CH:5]([OH:6])[CH:4]1[OH:3]

Participants

9

Reactant 5

HCID 971Oxalic AcidHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86757044HCID 86757044, compound

Product 1

HCID 77750336HCID 77750336, compoundYield 196.9%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 1, step (a) (1.6 g) in dimethylsulphoxide (15 ml) was treated with pyridine (0.25 g) followed by trifluoroacetic acid (0.18 g). To this mixture was added 1,3-dicyclohexylcarbodiimide (1.99 g). After stirring for 5 hours at the reaction mixture was treated with methyl(triphenylphosphoranylidene)acetate (1.72 g) and then stirred for a further 18 hours. The mixture was poured into ethyl acetate (300 ml) and treated with oxalic acid (1.59 g). After stirring for 30 minutes the mixture was filtered and the ethyl acetate solution was washed with dilute aqueous sodium bicarbonate and then with dilute aqueous brine, before being dried and concentrated. Purification (SiO2, ethyl acetate:isohexane 1:4 as eluant) afforded the subtitle compound (1.5 g).

Workup

  1. stirringstirred for a further 18 hours
  2. stirringAfter stirring for 30 minutes the mixture
  3. filtrationwas filtered
  4. washthe ethyl acetate solution was washed with dilute aqueous sodium bicarbonate
  5. dry with materialwith dilute aqueous brine, before being dried
  6. concentrationconcentrated
  7. customPurification (SiO2, ethyl acetate:isohexane 1:4 as eluant)

Sources & evidence

ORD record
ord-b7f45321fad14a83b83d8a91a023bb39
Source dataset
uspto-grants-2001_06
Patent number
US06251910B1

Reaction notes

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