Trifluoroacetic acid → (+/-)-{3-Chloro-6-[(4-fluoro-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-2,4b-diaza-fluoren-9-yl}-acetic acid methyl ester

HRID 1619490Notes

Reaction equation

HRID 1619490 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]([C:6]1[C:18]2[CH:17]=[N:16][C:15]([Cl:19])=[CH:14][C:13]=2[N:12]2[C:7]=1[CH2:8][CH2:9][CH:10]([N:20]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH3:21])[CH2:11]2)=O.C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:6]1[C:18]2[CH:17]=[N:16][C:15]([Cl:19])=[CH:14][C:13]=2[N:12]2[C:7]=1[CH2:8][CH2:9][CH:10]([N:20]([S:22]([C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)(=[O:24])=[O:23])[CH3:21])[CH2:11]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59471439(+/-)-{3-Chloro-6-[(4-fluoro-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-2,4b-diaza-fluoren-9-yl}-oxo-acetic acid methyl ester

Product 1

HCID 59471421(+/-)-{3-Chloro-6-[(4-fluoro-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-2,4b-diaza-fluoren-9-yl}-acetic acid methyl esterYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-{3-chloro-6-[(4-fluoro-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-2,4b-diaza-fluoren-9-yl}-oxo-acetic acid methyl ester (0.006 g) in 0.2 mL of CH2Cl2 were added 0.2 mL of TFA and 0.2 mL of Et3SiH. The reaction mixture was stirred overnight at r.t. and concentrated under vacuum. The residue was purified by silica gel chromatography eluted with 50% EtOAc/hexane to give 0.005 g desired product as a white solid. MS (ESI): 466.1. (M+1).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by silica gel chromatography
  3. washeluted with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-35b9a9aecd7b4b8e95d8c0586cb1dd95
Source dataset
uspto-grants-2014_07
Patent number
US08772312B2

Reaction notes

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