Acetic Acid → HCID 141573153, compound

HRID 1587724Notes

Reaction equation

HRID 1587724 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][C:27]([C:30]([OH:32])=[O:31])([CH3:29])[CH3:28])/[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18][NH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C([BH3-])#N.[Na+].[C:37]([OH:40])(=O)[CH3:38].[C:41]([O-:44])(=O)[CH3:42].[Na+]>CN(C=O)C.CO.O.C(#N)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][C:27]([C:30]([OH:32])=[O:31])([CH3:29])[CH3:28])/[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18][N:19]4[C:37](=[O:40])[CH2:38][CH:18]5[C:15](=[CH:14][C:20]([OH:21])=[C:41]([OH:44])[CH2:42]5)[CH2:16]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 88403825HCID 88403825, compound

Product 1

HCID 141573153HCID 141573153, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

The product from c) (210 mg) in DMF (1 ml) was added, at 0° C., to a suspension of 7-[2-(2-aminothiazol-4-yl)-2-((Z)-1-carboxy-1-methylethoxyimino)acetamido]-3-aminomethylceph-3-em-4-carboxylic acid (484 mg) in methanol/water (9:1 ratio; 7 ml) under an argon atmosphere. Sodium cyanoborohydride (63 mg) was added, reaction mixture was stirred for 3 hours at ambient temperature and solvent evaporated under reduced pressure to give a residue. This was dissolved in 10% aqueous acetonitrile (30 ml) containing acetic acid and sodium acetate and purified by preparative HPLC chromatography (Dynamax) using acetonitrile/water containing 0.1% trifluoroacetic acid as eluant to a carboxy-1-methylethoxyimino)acetamido]-3-(4,5-dihydroxy-2-(methoxycarbonylmethyl)benzylaminomethyl)ceph-3-em-4-carboxylic acid (50 mg); NMR (DMSO-d6 /CF3COOH) 1.50(s,3H); 1.53(s,3H); 3.63(s,3H); 3.7(m,2H); 3.92(m,2H); 4.1(m,2H); 5.22(d,1H); 5.9(dd,1H); 6.72(s,1H); 6.95(s,1H); 7.1(s,1H); 8.3(s,1H); 9.1(s,1H); 9.62(d,2H): FAB M/S (M-H)- 678.

Workup

  1. customreaction mixture
  2. customsolvent evaporated under reduced pressure
  3. customto give a residue
  4. custompurified by preparative HPLC chromatography (Dynamax)

Sources & evidence

ORD record
ord-69351728b1ef42e3a7179343cd8cefc9
Source dataset
uspto-grants-1993_06
Patent number
US05219848

Reaction notes

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