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

HRID 1619491
Notes
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Reaction equation

HRID 1619491 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[C:17]2[CH:16]=[N:15][C:14]([Cl:18])=[CH:13][C:12]=2[N:11]2[C:6]=1[CH2:7][CH2:8][CH:9]([N:19]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH3:20])[CH2:10]2.O.[Li+].[OH-].CC(O)=O>C1COCC1>[Cl:18][C:14]1[N:15]=[CH:16][C:17]2[C:5]([CH2:4][C:3]([OH:31])=[O:2])=[C:6]3[N:11]([C:12]=2[CH:13]=1)[CH2:10][CH:9]([N:19]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH3:20])[CH2:8][CH2:7]3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59471421(+/-)-{3-Chloro-6-[(4-fluoro-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-2,4b-diaza-fluoren-9-yl}-acetic acid methyl ester

Product 1

HCID 59471435(+/-)-{3-Chloro-6-[(4-fluoro-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-2,4b-diaza-fluoren-9-yl}-acetic acid
Yield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4 mg of (±)-{3-chloro-6-[(4-fluoro-benzenesulfonyl)-methyl-amino]-5,6,7,8-tetrahydro-2,4b-diaza-fluoren-9-yl}-acetic acid methyl ester in 0.2 mL of THF was added 0.1 mL of water, followed by 0.02 mL of 1 N aq. LiOH solution. After stirring for 1 h at room temperature, 0.05 mL of AcOH was added. The reaction mixture was the dried with a jet flow of nitrogen. The residue was suspended in 0.3 mL of EtOAc and filtered through silica gel. The filtrate was concentrated to give 2 mg of the title compound as a white solid. MS (ESI): 452.1 (M+1).

Workup

  1. customdried with a jet flow of nitrogen
  2. filtrationfiltered through silica gel
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-93df32f5e2fd4be992be5d355084d75c
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772312B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes