Sulfuric Acid → HCID 178483101, compound

HRID 1488772Notes

Reaction equation

[CH3:1][N:2]([C@@H:4]1[C:24](=[O:25])[C:23]([C:26]([NH2:28])=[O:27])=[C:22]([OH:29])[C@:21]2([OH:30])[C@H:5]1[CH2:6][C@H:7]1[C:18]([C:19]2=[O:20])=[C:17]([OH:31])[C:10]2[C:11]([OH:16])=[C:12](N)[CH:13]=[CH:14][C:9]=2[CH2:8]1)[CH3:3].Cl.S(=O)(=O)(O)O.[Cl:38][CH2:39][C:40]([O:42]C(=O)CCl)=O.[OH-].[NH4+:48]>CN(C)C=O.O>[Cl:38][CH2:39][C:40]([NH:48][C:4]1([N:2]([CH3:3])[CH3:1])[CH:5]2[C:21]([OH:30])([C:19]([OH:20])=[C:18]3[CH:7]([CH2:6]2)[CH2:8][C:9]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[C:17]3=[O:31])[C:22](=[O:29])[C:23]([C:26]([NH2:28])=[O:27])=[C:24]1[OH:25])=[O:42]

Participants

Conditions

Temperature: 0 °C

Procedure

Two and a half grams of 9-amino-6-demethyl-6-deoxytetracycline hydrochloride is added in portions, at 15°-20° C., to a solution of 17 ml of dimethylformamide and 0.6 ml of concentrated sulfuric acid. The added solid is completely in solution after 15 minutes. The solution is then cooled to 0° C. and 2.3 g of chloroacetic anhydride in 5 ml of dimethylformamide is added, dropwise, while maintaining the temperature at 0°-2° C. The reaction mixture is stirred for 30 minutes, poured into 40 g of ice and 35 ml of water, and the pH is adjusted to pH 5.34 with concentrated ammonium hydroxide. The resulting solid is stirred for 30 minutes, collected, washed 2× with water, washed 2× acetone and dried in vacuo to give 2.4 g of the desired intermediate.

Workup

temperaturedropwise, while maintaining the temperature at 0°-2° C
stirringThe resulting solid is stirred for 30 minutes
customcollected
washwashed 2× with water
washwashed 2× acetone
customdried in vacuo

Sources & evidence

ORD record: ord-d20681633e2f472da2ad4cecb45d8d9f
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05675030

Reaction notes

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