Diisopropyl Ether → HCID 131712710, compound

HRID 2295934Notes

Reaction equation

HRID 2295934 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31](=[O:63])[C:32]([C:38]3[N:39]=[C:40]([NH:43][C:44]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[S:41][CH:42]=3)=[N:33][O:34][CH2:35][CH2:36][I:37])[C:28](=[O:64])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2].[NH2:65][C:66](N)=[S:67].C(OC(C)C)(C)C.C[N:77](P(N(C)C)(N(C)C)=O)C>>[IH:37].[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([NH:30][C:31](=[O:63])[C:32]([C:38]3[N:39]=[C:40]([NH:43][C:44]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[S:41][CH:42]=3)=[N:33][O:34][CH2:35][CH2:36][S:67][CH:66]=[N:65][NH2:77])[C:28](=[O:64])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 7914Diisopropyl EtherHCID 12679HexamethylphosphoramideHCID 2723790ThioureaHCID 131712712HCID 131712712, compound

Product 1

HCID 131712710HCID 131712710, compound

Procedure

A mixture of 870 mg of the syn isomer of benzhydryl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-iodoethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate [described in Belgium patent No. 875,217], 131 mg of thiourea and 1.7 ml of anhydrous hexamethylphosphorotriamide was stirred for 32 hours and 75 ml of isopropyl ether were added thereto with stirring. The mixture was decanted and 45 ml of ethyl ether were added thereto. The mixture was vacuum filtered to obtain 1.229 g of solvated syn isomer of benzhydryl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-aminoiminomethylthioethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate hydroiodide melting at ≃100° C.

Workup

  1. customThe mixture was decanted
  2. addition45 ml of ethyl ether were added
  3. filtrationfiltered

Sources & evidence

ORD record
ord-28f7b228bc044478a615184a30246775
Source dataset
uspto-grants-1984_01
Patent number
US04426519

Reaction notes

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