Water → 7-[2-(2-Tritylamino-4-thiazolyl)-acetamido]-3-acetylthiomethyl-ceph-3-eme-4-carboxylic acid

HRID 839924Notes

Reaction equation

[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([CH2:26][C:27]([NH:29][CH:30]2[C:45](=[O:46])[N:32]3[C:33]([C:42]([OH:44])=[O:43])=[C:34]([CH2:37]OC(=O)C)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[C:52]([O-:55])(=[S:54])[CH3:53].[K+].O>C(O)(=O)C.CC(C)=O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([CH2:26][C:27]([NH:29][CH:30]2[C:45](=[O:46])[N:32]3[C:33]([C:42]([OH:44])=[O:43])=[C:34]([CH2:37][S:54][C:52](=[O:55])[CH3:53])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1.63 of the product of Step B, 0.21 g of sodium bicarbonate, 0.66 g of potassium thioacetate, 10 ml of water and 5 ml of acetone was heated at 90° C for 21/2 hours and was then acidified with 1 ml of acetic acid. The mixture was vacuum filtered and the solid product was washed and chromatographed over silica gel. Elution with a 1-1 methylene chloride-ether mixture and then with a 5-1-4 acetone-water-ether mixture yielded 830 mg of 7-[2-(2-tritylamino-4-thiazolyl)-acetamido]-3-acetylthiomethyl-ceph-3-eme-4-carboxylic acid.

Workup

filtrationfiltered
washthe solid product was washed
customchromatographed over silica gel
washElution with a 1-1 methylene chloride-ether mixture

Sources & evidence

ORD record: ord-a2acf45bb2ac41cba4cbb8976d2a3219
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04097595

Reaction notes

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