Trifluoroacetic acid → HCID 136433448, compound

HRID 1589821Notes

Reaction equation

HRID 1589821 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:43]/[O:44][C:45](OC(C)(C)C)([CH3:50])[CH2:46]C(O)=O)/[C:8]([NH:10][CH:11]2[C:41](=[O:42])[N:13]3[C:14]([C:38]([OH:40])=[O:39])=[C:15]([CH2:18][S:19][C:20]4[N:24]([C:25]5[CH:30]=[C:29]([OH:31])[C:28]([OH:32])=[C:27]([Cl:33])[C:26]=5[CH2:34][C:35]([OH:37])=[O:36])[N:23]=[N:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)[C:58]([OH:60])=[O:59]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:43]/[O:44][C:45]([C:58]([OH:60])=[O:59])([CH3:50])[CH3:46])/[C:8]([NH:10][CH:11]2[C:41](=[O:42])[N:13]3[C:14]([C:38]([OH:40])=[O:39])=[C:15]([CH2:18][S:19][C:20]4[N:24]([C:25]5[CH:30]=[C:29]([OH:31])[C:28]([OH:32])=[C:27]([Cl:33])[C:26]=5[CH2:34][C:35]([OH:37])=[O:36])[N:23]=[N:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 172974452HCID 172974452, compound

Product 1

HCID 136433448HCID 136433448, compound

Procedure

7-[2-(2-Aminothiazol-4-yl)-2-((Z)-1-t-butoxycarboxy-1-methyl ethoxyimino)acetamido]-3-[(1-(2-carboxymethyl-3-chloro-4,5-dihydroxyphenyl)-tetrazol-5-yl)thiomethyl]ceph-3-em-4-carboxylic acid (0.875 g) was treated with trifluoroacetic acid (10 ml) at room temperature for 1 hour. The mixture was evaporated and the residue triturated with ether to give a solid which was collected by filtration and purified by HPLC (AMICON C18 15 μm), eluting with methanol/water/acetic acid (35:65:1 to 40:60:1) [Dimethylformamide was necessary for dissolution of the crude product.] Thus was obtained the title product (0.38 g); NMR (DMSO-d6 /CD3CO2D/CF3CO2D) 1.55(s,6H, --C(CH3)2 --); 3.35(s,2H,--CH2COOH); 3.60 and 3.85(2d, J=18 Hz, --SCH2 --); 4.30 and 4.65 (2d,J=11.5 Hz, 2H, --CH2 --S--tetrazole); 5.20 and 5.85(2d, J=4.5 Hz, 2H, H6 and H7); 6.85 (s,1H, aromatic); 7.05(s,1H, thiazole).

Workup

  1. customThe mixture was evaporated
  2. customthe residue triturated with ether
  3. customto give a solid which
  4. filtrationwas collected by filtration
  5. custompurified by HPLC (AMICON C18 15 μm)
  6. washeluting with methanol/water/acetic acid (35:65:1 to 40:60:1) [Dimethylformamide
  7. dissolutionwas necessary for dissolution of the crude product

Sources & evidence

ORD record
ord-24f495f0c0564389ae5fc7fb6c395e31
Source dataset
uspto-grants-1993_04
Patent number
US05200404

Reaction notes

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