(-)-Mandelic acid → (2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide(R)-(-)-mandelate

HRID 1887768Notes

Reaction equation

HRID 1887768 reaction equation
[NH2:1][C:2]([CH3:38])([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:8])=[O:4].[C:39]([OH:49])(=[O:48])[C@@H:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[OH:41]>C1(C)C=CC=CC=1.C(O)(C)C>[C:39]([OH:49])(=[O:48])[C@@H:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[OH:41].[NH2:1][C:2]([CH3:37])([CH3:38])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:8])=[O:4]

Participants

5

Reactant 2

HCID 11914(-)-Mandelic acidHCID 59620332(2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

Product 1

HCID 89723348(2R)-2-(2-amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide(R)-(-)-mandelate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

(2R)-2-(2-Amino-2-methylpropanamido)-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide (540 mg) was dissolved in toluene (5.4 mL), and a solution of D-(−)-mandelic acid (152 mg) in isopropanol (1.6 mL) was added thereto, followed by stirring at room temperature for 18 hours. The formed precipitates were recovered through filtration, washed with a mixture of toluene and isopropanol (1:1), and dried under reduced pressure, whereby the title compound (502 mg) was yielded.

Workup

  1. customThe formed precipitates
  2. filtrationwere recovered through filtration
  3. washwashed with a mixture of toluene and isopropanol (1:1)
  4. dry with materialdried under reduced pressure, whereby the title compound (502 mg)
  5. customwas yielded

Sources & evidence

ORD record
ord-4949177b8d0b44508281ae25318b9233
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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