HCID 86588220, compound → HCID 86588222, compound

HRID 1814328Notes

Reaction equation

HRID 1814328 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][C@H:8]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:17][C:16]=1[O:26][CH2:27][CH2:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)(=[O:14])=[O:13])[CH:9]=[O:10])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:29]1([CH2:28][CH2:27][O:26][C:16]2[CH:17]=[C:18]([N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)[CH:19]=[CH:20][C:15]=2[S:12]([NH:11][C@H:8]([CH:9]=[O:10])[CH2:7][C:6]([OH:39])=[O:5])(=[O:13])=[O:14])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 86588220HCID 86588220, compound

Product 1

HCID 86588222HCID 86588222, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (S)-3-[2-(2-naphthalen-1-yl-ethoxy)-4-pyrrolidin-1-yl-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester (0.60 g, 1.10 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 linear gradient of water containing 0.1% TFA and acetonitrile containing 0.1% TFA (20-65% acetonitrile, in 120 min) at a flow rate of 20 mL/min. Fractions containing the major peak were pooled and lyophilized to yield 0.190 g (60%) of (S)-3-[2-(2-naphthalen-1-yl-ethoxy)-4-pyrrolidin-1-yl-benzenesulfonyl amino]-4-oxo-butyric acid. MS (APCI) m/z 496.1 (M+1).

Workup

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

Sources & evidence

ORD record
ord-e31804b7585247a2b2d7662388a435fc
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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