Sulfuric Acid → HCID 178418608, compound

HRID 6443Notes

Reaction equation

HRID 6443 reaction equation
[CH3:1][N:2]([CH:4]1[C:23](=[O:24])[C:22]([C:25]([NH2:27])=[O:26])=[C:21]([OH:28])[C:20]2([OH:29])[CH:5]1[CH2:6][CH:7]1[C:17]([C:18]2=[O:19])=[C:16]([OH:30])[C:10]2[C:11]([OH:15])=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8]1)[CH3:3].[Br:31]N1C(=O)CCC1=O.C(OCC)C.[S:44](=[O:48])(=[O:47])([OH:46])[OH:45]>>[S:44]([OH:48])([OH:47])(=[O:46])=[O:45].[Br:31][C:14]1[CH:13]=[CH:12][C:11]([OH:15])=[C:10]2[C:9]=1[CH2:8][CH:7]1[C:17]([C:16]2=[O:30])=[C:18]([OH:19])[C:20]2([OH:29])[CH:5]([CH:4]([N:2]([CH3:1])[CH3:3])[C:23]([OH:24])=[C:22]([C:25]([NH2:27])=[O:26])[C:21]2=[O:28])[CH2:6]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 54680104HCID 54680104, compound

Product 1

HCID 178418608HCID 178418608, compound

Conditions

Temperature
0 °C

Procedure

A solution of 4.14. g of 6-demethyl-6-deoxytetracycline, prepared by the described literature procedure, and 1.99 g of N-bromosuccinimide dissolved in 50 ml of concentrated sulfuric acid is stirred at 0° C. for 45 minutes or until solution occurs. The reaction mixture is added dropwise to 2 L of cold diethyl ether. The resulting precipitate is collected and dried. The solid is dissolved in 2-methoxyethanol, triturated with methanol, collected, washed with methanol and diethyl ether and dried to give 6.22 g of crude product. The solid is recrystallized from 2-methoxyethanol and methanol to give 3.1 g of pure product. MS(FAB): m/z 493 (M+H). 1H NMR(CD3SOCD3): δ 4.3(s, lH, 4-H), 6.8(d, lH, 9-H) and 7.75(d, IH, 8-H).

Workup

  1. customThe resulting precipitate is collected
  2. customdried
  3. dissolutionThe solid is dissolved in 2-methoxyethanol
  4. customtriturated with methanol
  5. customcollected
  6. washwashed with methanol and diethyl ether
  7. customdried
  8. customto give 6.22 g of crude product
  9. customThe solid is recrystallized from 2-methoxyethanol and methanol

Sources & evidence

ORD record
ord-c5f43a80403f4b4babc1305c8508f598
Source dataset
uspto-grants-1993_09
Patent number
US05248797

Reaction notes

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