Trifluoroacetic acid → HCID 88519921, compound

HRID 2231988Notes

Reaction equation

HRID 2231988 reaction equation
C([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:73])[C@@H:15]([NH:16][C:17](=[O:72])/[C:18](/[C:47]3[N:48]=[C:49]([NH:52]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:50][CH:51]=3)=[N:19]\[O:20][CH2:21][C:22]3[N:23]=[C:24]([NH:27]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:25][CH:26]=3)[C@H:12]2[S:11][CH2:10][C:9]=1[CH2:74][O:75][C:76](=[O:78])[CH3:77])=[O:7])(C)(C)C.[F:79][C:80]([F:85])([F:84])[C:81]([OH:83])=[O:82].C(OC(C)C)(C)C>C1(OC)C=CC=CC=1>[F:79][C:80]([F:85])([F:84])[C:81]([OH:83])=[O:82].[NH2:52][C:49]1[S:50][CH:51]=[C:47](/[C:18](=[N:19]/[O:20][CH2:21][C:22]2[N:23]=[C:24]([NH2:27])[S:25][CH:26]=2)/[C:17]([NH:16][C@@H:15]2[C:14](=[O:73])[N:13]3[C:8]([C:6]([OH:7])=[O:5])=[C:9]([CH2:74][O:75][C:76](=[O:78])[CH3:77])[CH2:10][S:11][C@H:12]23)=[O:72])[N:48]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 88519909HCID 88519909, compound

Product 1

HCID 88519921HCID 88519921, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

2.3 g of the (6R,7R)-7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-tritylaminothiazol-4-yl)methoxyimino]acetamido]-3-(acetoxymethyl)-ceph-3-em-4-carboxylic acid t-butyl ester was suspended in 2.1 ml of anisole, 21 ml of trifluoroacetic acid was added with ice cooling, and reacted at the same temperature for about 3 hours. After the completion of the reaction, the reaction mixture was poured into 200 ml of isopropyl ether with ice cooling, and the supernatant was removed. The residue was washed thoroughly with isopropyl ether, and the precipitates were filtered off to obtain 1.4 g of (6R,7R)-7-[(Z)-2-(2-aminothiazol-4-yl)-2-[(2-aminothiazol-4-yl)methoxyimino]acetamido]-3-(acetoxymethyl)-ceph-3-em-4-carboxylic acid trifluoroacetate.

Workup

  1. customreacted at the same temperature for about 3 hours
  2. customAfter the completion of the reaction
  3. customthe supernatant was removed
  4. washThe residue was washed thoroughly with isopropyl ether
  5. filtrationthe precipitates were filtered off

Sources & evidence

ORD record
ord-b69e2ac0c4064363adf5cc041a716f5d
Source dataset
uspto-grants-1988_11
Patent number
US04785090

Reaction notes

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