Sodium Hydroxide → HCID 86608947, compound

HRID 1985730Notes

Reaction equation

HRID 1985730 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22]Br)=[C:14]([Br:24])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NC(N)=[S:27].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH2:22][SH:27])=[C:14]([Br:24])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 69067664HCID 69067664, compound

Product 1

HCID 86608947HCID 86608947, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 0.90 g (4R,9aR)-7-bromo-6-bromomethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 10 ml ethanol was added at room temperature 0.2 g thiourea and the mixture was stirred at ambient temperature for 5 h. To the resulting clear solution was added 1 ml of 2N aqueous sodium hydroxide and the mixture was heated to reflux for 3 h. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=9:1 to yield 0.51 g of the title compound as crystalline solid (MS: 414.1 and 416.2 (M+H+)).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. custompartitioned between water and ethyl acetate
  5. customThe phases were separated
  6. customthe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-5d6ee1f1c81646fdbb16a61822f6f65f
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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