Diethyl Ether → HCID 131712154, compound

HRID 848755Notes

Reaction equation

HRID 848755 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH3:6][N:7]1[C:11]([S:12][CH2:13][C:14]2[CH2:15][S:16][C@@H:17]3[CH:24]([NH:25][C:26](=[O:60])[C:27]([C:35]4[N:36]=[C:37]([NH:40][C:41]([C:54]5[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=5)([C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)[C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[S:38][CH:39]=4)=[N:28][O:29][C:30]([CH3:34])([O:32][CH3:33])[CH3:31])[C:23](=[O:61])[N:18]3[C:19]=2[C:20]([OH:22])=[O:21])=[N:10][N:9]=[N:8]1.CCOCC>C(OCC)(=O)C>[CH3:6][N:7]1[C:11]([S:12][CH2:13][C:14]2[CH2:15][S:16][C@@H:17]3[CH:24]([NH:25][C:26](=[O:60])[C:27]([C:35]4[N:36]=[C:37]([NH:40][C:41]([C:54]5[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=5)([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)[S:38][CH:39]=4)=[N:28][O:29][C:30]([CH3:34])([O:32][CH3:33])[CH3:31])[C:23](=[O:61])[N:18]3[C:19]=2[C:20]([OH:22])=[O:21])=[N:10][N:9]=[N:8]1.[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2]

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

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

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-db5ed48001b1480092fb9ed79b78da2b
Source dataset
uspto-grants-1981_10
Patent number
US04297352

Reaction notes

Loading…