Dichloromethane → HCID 131713457, compound

HRID 1904128Notes

Reaction equation

HRID 1904128 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:47])[C:19]([C:22]3[N:23]=[C:24]([NH:27][C:28]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[S:25][CH:26]=3)=[N:20][OH:21])[C:15](=[O:48])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(Cl)Cl.[C:52](Cl)(=[O:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[CH2:61]([NH:63][CH2:64][CH3:65])[CH3:62]>C(OCC)(=O)C.N1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:47])[C:19]([C:22]3[N:23]=[C:24]([NH:27][C:28]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[S:25][CH:26]=3)=[N:20][O:21][C:52]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[O:59])[C:15](=[O:48])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].[CH2:61]([NH:63][CH2:64][CH3:65])[CH3:62]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 8021DiethylamineHCID 131712517HCID 131712517, compound

Product 1

HCID 131713457HCID 131713457, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.683 g of the syn isomer of 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(hydroxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid, 10 ml of methylene chloride, 0.2 ml of pyridine and 0.2 ml of benzoyl chloride was stirred at room temperature for 10 minutes and was washed with water acidified to a pH of 1. The organic phase was dried, vacuum filtered and evaporated to dryness to obtain 0.737 g of raw product. The latter was dissolved in 5 ml of ethyl acetate and 0.1 ml of diethylamine was added thereto. After 10 minutes, the mixture was vacuum filtered to obtain 0.27 g of the syn isomer of diethylamine 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(phenylcarbonyloxyimino)-acetamido]-ceph-3-eme-4-carboxylate.

Workup

  1. washwas washed with water
  2. customThe organic phase was dried
  3. filtrationvacuum filtered
  4. customevaporated to dryness
  5. customto obtain 0.737 g of raw product
  6. waitAfter 10 minutes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-0ca1c9f6b89843ac9e2bc11a0c7691d0
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

Loading…