Diethyl Ether → HCID 131712154, compound

HRID 1577159Notes

Reaction equation

HRID 1577159 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]([NH:20][C:21](=[O:55])[C:22]([C:30]4[N:31]=[C:32]([NH:35][C:36]([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)([C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)[C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[S:33][CH:34]=4)=[N:23][O:24][C:25]([CH3:29])([O:27][CH3:28])[CH3:26])[C:18](=[O:56])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1.[CH2:57]([NH:59][CH2:60][CH3:61])[CH3:58].CCOCC>C(OCC)(=O)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:21](=[O:55])[C:22]([C:30]4[N:31]=[C:32]([NH:35][C:36]([C:49]5[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=5)([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)[S:33][CH:34]=4)=[N:23][O:24][C:25]([CH3:29])([O:27][CH3:28])[CH3:26])[C:18](=[O:56])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1.[CH2:57]([NH:59][CH2:60][CH3:61])[CH3:58]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8021DiethylamineHCID 131712155HCID 131712155, compound

Product 1

HCID 131712154HCID 131712154, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Step A was taken up in 10 ml of ethyl acetate and 0.5 ml of diethylamine were added thereto. 100 ml of ether were added to the mixture which was vacuum filtered to obtain 2.748 g of the syn isomer of diethylamine 3-[(1-methyl-tetrazol-5-yl)-thiomethyl]-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxy-ethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate which was added to 10 ml of acetone and 3.5 ml of N hydrochloric acid. The mixture was stirred for 40 minutes and the acetone was evaporated. The mixture was extracted with ethyl acetate and the organic phase was dried and evaporated to a small volume. 50 ml of ether were added thereto and the mixture was vacuum filtered to obtain 1.83 g of the syn isomer of 3-[(1-methyl-tetrazol-5-yl)-thiomethyl]-7-[2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-2c90d91fb11b457fb381747e1fb3ce7c
Source dataset
uspto-grants-1981_09
Patent number
US04287193

Reaction notes

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