Hydrochloric Acid → HCID 131713473, compound

HRID 1904144Notes

Reaction equation

HRID 1904144 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH2:20])[C:18](=[O:21])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1.C(Cl)Cl.[N:25]([CH2:28][CH2:29][O:30][N:31]=[C:32]([C:36]1[N:37]=[C:38]([NH:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:39][CH:40]=1)[C:33](O)=[O:34])=[N+:26]=[N-:27].ON1C2C=CC=CC=2N=N1.Cl>O.C(N(CC)CC)C>[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:33](=[O:34])[C:32]([C:36]4[N:37]=[C:38]([NH:41][C:42]([C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=5)([C:55]5[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=5)[C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)[S:39][CH:40]=4)=[N:31][O:30][CH2:29][CH2:28][N:25]=[N+:26]=[N-:27])[C:18](=[O:21])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidHCID 73708098HCID 73708098, compound

Product 1

HCID 131713473HCID 131713473, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 0.652 g of 3-[(1-methyl-1H-tetrazol-5-yl)-thiomethyl]-7-amino-ceph-3-eme-4-carboxylic acid, 6.5 ml of methylene chloride and 0.56 ml of triethylamine was stirred at room temperature for 15 minutes and then 1.29 g of 1-hydroxy-1H-benzotriazole 2-(2-azidoethoxyimino)-2-(2-tritylamino-4-thiazolyl)-acetate were added thereto. The mixture was stirred at room temperature for 20 hours and then 10 ml of water and 3 ml of 2 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 5 ml of ethyl acetate and 10 ml of ether were added thereto. The mixture was stirred for 30 minutes at room temperature and was vacuum filtered to obtain 1.416 g of raw syn isomer of 3-[(1-methyl-1H-tetrazol-5-yl)-thiomethyl]-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-azidoethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 hours
  2. washThe decanted organic phase was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. addition10 ml of ether were added
  6. stirringThe mixture was stirred for 30 minutes at room temperature
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7fab48e633b0485ca149be8eb642fef0
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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