Hydrazine hydrate (1:1) → HCID 178438829, compound

HRID 402747Notes

Reaction equation

HRID 402747 reaction equation
[P:1]([O:19][C:20]1[C:40]([CH:41]([CH3:43])[CH3:42])=[CH:39][C:23]2[C:24](=S)[N:25]([C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[CH2:34][CH2:33][CH2:32]4)[C:26](=[O:28])[O:27][C:22]=2[CH:21]=1)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].O.[NH2:45][NH2:46]>C(O)C>[P:1]([O:19][C:20]1[CH:21]=[C:22]([OH:27])[C:23]([C:24]2[N:25]([C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[CH2:34][CH2:33][CH2:32]4)[C:26]([OH:28])=[N:46][N:45]=2)=[CH:39][C:40]=1[CH:41]([CH3:43])[CH3:42])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86762470dibenzyl 3-(2,3-dihydro-1H-inden-5-yl)-6-isopropyl-2-oxo-4-thioxo-3,4-dihydro-2H-benzo[e][1,3]oxazin-7-yl phosphate

Product 1

HCID 178438829HCID 178438829, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 0.52 g (0.84 mmols) of 7 in 15 mL of anhydrous ethanol was added 63 mg (1.27 mmols) of hydrazine hydrate and the mixture stirred at 80° C. for 30 min. The mixture was concentrated and chromatographed on silica gel using 1:1 hexane:ethylacetate to afford 0.16 g of the product 8 as off-white foam.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed on silica gel using 1:1 hexane

Sources & evidence

ORD record
ord-b698c4c7a3534d83be105b9145da7c19
Source dataset
uspto-grants-2014_06
Patent number
US08742133B2

Reaction notes

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