Hydrochloric Acid → HCID 131713466, compound

HRID 1904139Notes

Reaction equation

HRID 1904139 reaction equation
[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=[O:3].C(Cl)Cl.[C:22]([NH:41][C:42]1[S:43][CH:44]=[C:45]([C:47](=[N:51][O:52][CH2:53][CH2:54][N:55]=[N+:56]=[N-:57])[C:48](O)=[O:49])[N:46]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.ON1C2C=CC=CC=2N=N1.Cl>O.C(N(CC)CC)C>[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[CH:10]([NH:13][C:48](=[O:49])[C:47]([C:45]3[N:46]=[C:42]([NH:41][C:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[S:43][CH:44]=3)=[N:51][O:52][CH2:53][CH2:54][N:55]=[N+:56]=[N-:57])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])(=[O:3])[CH3:1].[CH2:7]([NH:8][CH2:9][CH3:10])[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 4413287-Aminocephalosporanic acidHCID 73708098HCID 73708098, compound

Product 1

HCID 131713466HCID 131713466, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2.54 g of 7-amino-cephalosporanic acid, 25 ml of anhydrous methylene chloride and 2.6 ml of triethylamine was stirred at room temperature for 15 minutes and then 6.02 g of 1-hydroxy-1H-benzotriazole 2-(2-tritylamino-4-thiazolyl)-2-(2-azidoethoxyimino)-acetate were added thereto. The mixture was stirred at room temperature for 45 hours and 25 ml of water and 5 ml of N hydrochloric acid were added thereto. The decanted organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was taken up in 30 ml of ethyl acetate and 2.4 ml of diethylamino were added to the solution. The mixture was cooled at 0° C. and was vacuum filtered to obtain 5.9 g of the syn isomer of diethylamine 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-azidoethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate.

Workup

  1. stirringThe mixture was stirred at room temperature for 45 hours
  2. washThe decanted organic phase was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. addition2.4 ml of diethylamino were added to the solution
  6. temperatureThe mixture was cooled at 0° C.
  7. filtrationfiltered

Sources & evidence

ORD record
ord-54671b300a214ec4936cf6ba584e6964
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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