HCID 86588211, compound → HCID 86588210, compound

HRID 1814304Notes

Reaction equation

HRID 1814304 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][C@H:8]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][C:16]=1[O:24][CH2:25][CH2:26][C:27]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:28]=1[CH:29]=[CH:30][CH:31]=[N:32]2)(=[O:14])=[O:13])[CH:9]=[O:10])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:23][N:21]([CH3:22])[C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][C@H:8]([CH:9]=[O:10])[CH2:7][C:6]([OH:37])=[O:5])(=[O:13])=[O:14])=[C:16]([O:24][CH2:25][CH2:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH:29]=[CH:30][CH:31]=[N:32]3)[CH:17]=1

Participants

4

Reactant 1

HCID 86588211HCID 86588211, compound

Product 1

HCID 86588210HCID 86588210, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (S)-3-[4-dimethylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester (0.33 g, 0.60 mmol) in TFA (2 mL) and CH2Cl2 (20 mL) was stirred for 3 h. After the solvent was removed under vacuum, the residue was subjected to preparative reverse-phase HPLC (VYDAC, C18) using a linear gradient of (A) water containing 0.1% TFA and (B) acetonitrile containing 0.1% TFA (20-65% B, in 120 min) at a flow rate of 15 mL/min. Fractions containing the major peak were pooled and lyophilized to yield 0.260 g (92%) of (S)-3-[4-dimethylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid. MS (APCI) m/z 470.1 (M−1).

Workup

  1. customAfter the solvent was removed under vacuum
  2. customa linear gradient of (A) water containing 0.1% TFA and (B) acetonitrile containing 0.1% TFA (20-65% B, in 120 min)
  3. additionFractions containing the major peak

Sources & evidence

ORD record
ord-593a04c8b13e4309a52777ca15be3905
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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