HCID 69692575, compound → HCID 69692523, compound

HRID 1814349Notes

Reaction equation

HRID 1814349 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][C@H:8]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][C:16]=1[O:25][CH2:26][CH2:27][C:28]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[N:33]2)(=[O:14])=[O:13])[C:9]#[N:10])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][C@H:8]([C:9]#[N:10])[CH2:7][C:6]([OH:38])=[O:5])(=[O:14])=[O:13])=[C:16]([O:25][CH2:26][CH2:27][C:28]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:29]=2[CH:30]=[CH:31][CH:32]=[N:33]3)[CH:17]=1)(=[O:24])[CH3:23]

Participants

4

Reactant 1

HCID 69692575HCID 69692575, compound

Product 1

HCID 69692523HCID 69692523, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (S)-3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-3-cyano-propionic acid tert-butyl ester (0.20 g, 0.40 mmol) in TFA (2 mL) and CH2Cl2 (20 mL) was stirred for 9 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 (3) acetonitrile containing 0.1% TFA (0-40% B, in 120 min) at a flow rate of 15 mL/min. Fractions containing the major peak were pooled and lyophilized to yield 50 mg (26%) of (S)-3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-3-cyano-propionic acid. MS (APCI) m/z 483.1 (M+1).

Workup

  1. customAfter the solvent was removed under vacuum
  2. customa linear gradient of (A) water containing 0.1% TFA and (3) acetonitrile containing 0.1% TFA (0-40% B, in 120 min)
  3. additionFractions containing the major peak

Sources & evidence

ORD record
ord-34a42ba36728406d8644954e7f603556
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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