Hydrazine hydrate (1:1) → HCID 54443208, compound

HRID 375761Notes

Reaction equation

HRID 375761 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:33])[C:5]2[CH2:16][S:15][CH2:14][C@@H:13]([C:17](OC)=[O:18])[NH:12][C:11](=[O:21])[C@@H:10]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:9][O:8][C:7](=[O:30])[C:6]=2[C:31]=1[CH3:32].O.[NH2:35][NH2:36]>CO.C(OCC)(=O)C>[C:17]([C@H:13]1[NH:12][C:11](=[O:21])[C@@H:10]([NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:9][O:8][C:7](=[O:30])[C:6]2[C:31]([CH3:32])=[C:2]([OH:1])[CH:3]=[C:4]([OH:33])[C:5]=2[CH2:16][S:15][CH2:14]1)(=[O:18])[NH:35][NH2:36]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 12967658HCID 12967658, compound

Product 1

HCID 54443208HCID 54443208, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 97 mg of the product of Example 2 and 0.2 ml of hydrazine hydrate in 1 ml of methanol was stirred at 20° C. for 45 minutes. The solution was diluted with ethyl acetate, and washed with 0.5M sodium dihydrogenphosphate solution and with water. The organic layer was dried over sodium sulfate and evaporated in vacuo, and the residue was crystallized from methanol/ethyl acetate/hexane to give 85 mg of tert-butyl (4R, 7S)-4-carbazoyl-1,3,4,5,6,7,8,10-octahydro-12,14-dihydroxy-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as a white solid. as a white solid.

Workup

  1. washwashed with 0.5M sodium dihydrogenphosphate solution and with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customthe residue was crystallized from methanol/ethyl acetate/hexane

Sources & evidence

ORD record
ord-077b24c0f19646f2a7116fde259c0775
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

Loading…