HCID 86608946, compound → HCID 11997661, compound

HRID 1985728Notes

Reaction equation

HRID 1985728 reaction equation
C(OC([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][S:23]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:14]([CH:43]=O)[CH:13]=3)[CH2:9]1)=O)(C)(C)C>C(O)=O>[NH3:8].[CH3:21][C@@H:19]1[CH2:20][NH:8][CH2:9][C@@H:10]2[N:18]1[C:17]1[N:16]=[C:15]3[CH2:22][S:23][CH2:43][C:14]3=[CH:13][C:12]=1[CH2:11]2

Participants

4

Reactant 1

HCID 86608946HCID 86608946, compound

Product 2

HCID 222AmmoniaHCID 11997661HCID 11997661, compoundYield 166.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 0.270 g (4R,9aR)-7-formyl-4-methyl-6-tritylsulfanylmethyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 5 ml 90% aqueous formic acid was kept at room temperature for 6 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the aqueous phase was mixed with dichloromethane. The pH of the mixture was adjusted to 12.00 by addition of 2N aqueous sodium hydroxide and the phases were separated. The organic phase was evaporated and the residue was purified by chromatography on silica gel with dichloromethane:methanol:ammonia=90:10:1 to yield 0.092 g of the title compound as brownish solid (MS: 246.3 (M+H+)).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe phases were separated
  3. additionthe aqueous phase was mixed with dichloromethane
  4. additionThe pH of the mixture was adjusted to 12.00 by addition of 2N aqueous sodium hydroxide
  5. customthe phases were separated
  6. customThe organic phase was evaporated
  7. customthe residue was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-8990747220b14c14ac6e860423793fef
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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