Diisopropyl Ether → HCID 131713450, compound

HRID 1904120Notes

Reaction equation

HRID 1904120 reaction equation
[C:1]1(=[O:15])[N:5]([CH2:6][C:7](Cl)=[O:8])[C:4](=[O:10])[C:3]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:2]12.[C:16]([O:19][CH2:20][C:21]1[CH2:22][S:23][C@@H:24]2[CH:31]([NH:32][C:33](=[O:62])[C:34]([C:37]3[N:38]=[C:39]([NH:42]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:40][CH:41]=3)=[N:35][OH:36])[C:30](=[O:63])[N:25]2[C:26]=1[C:27]([OH:29])=[O:28])(=[O:18])[CH3:17].C(NCC)C.C(OC(C)C)(C)C.C(O)=O.O>C(Cl)Cl.O>[C:16]([O:19][CH2:20][C:21]1[CH2:22][S:23][C@@H:24]2[CH:31]([NH:32][C:33](=[O:62])[C:34](=[N:35][O:36][C:7](=[O:8])[CH2:6][N:5]3[C:4](=[O:10])[C:3]4=[CH:11][CH:12]=[CH:13][CH:14]=[C:2]4[C:1]3=[O:15])[C:37]3[N:38]=[C:39]([NH2:42])[S:40][CH:41]=3)[C:30](=[O:63])[N:25]2[C:26]=1[C:27]([OH:29])=[O:28])(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 18673298Formic acid--water (1/1)HCID 131712516HCID 131712516, compound

Product 1

HCID 131713450HCID 131713450, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.335 g of phthalimidoacetyl chloride were added to a suspension of 0.756 g of the syn isomer of diethylamine 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylate in 4 ml of methylene chloride and after standing at room temperature for 5 minutes, 10 ml of isopropyl ether was added to the mixture. The mixture was vacuum filtered and the recovered product was empasted with water and was dried to obtain a raw product. The product in 2 ml of a 2-1 formic acid-water mixture was stirred for 20 minutes at 35°-40° C. and 10 ml of water was added thereto. The mixture was vacuum filtered and the product was taken up in ether and vacuum filtered again. The product was dried and dissolved in 4 ml of acetone. The mixture was vaccum dried and was crystallization from 10 ml of ether to obtain 0.280 g of the syn isomer of 3-acetoxymethyl-7-[2 -(2-amino-4-thiazolyl)-2-phthalimidoacetoxyiminoacetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. filtrationfiltered
  2. customwas dried
  3. customto obtain a raw product
  4. filtrationfiltered
  5. filtrationvacuum filtered again
  6. customThe product was dried
  7. dissolutiondissolved in 4 ml of acetone
  8. customThe mixture was vaccum dried
  9. customcrystallization from 10 ml of ether

Sources & evidence

ORD record
ord-e1a05213c637453bb07fbcf230c86f3e
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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