Terephthaloyl chloride → Trifluoroacetic acid

HRID 2382411Notes

Reaction equation

HRID 2382411 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]1([CH:14]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH2:15][NH:16][C:17]2[N:25]=[C:24]([N:26]3[CH2:30][CH2:29][C@@H:28]([NH:31][C:32]([NH:34][C@@H:35]4[CH2:39][CH2:38][NH:37][CH2:36]4)=[O:33])[CH2:27]3)[N:23]=[C:22]3[C:18]=2[N:19]=[CH:20][N:21]3[C@@H:40]2[CH2:44][C@H:43]([NH:45][C:46](=[O:49])[CH2:47][CH3:48])[C@@H:42]([OH:50])[C@H:41]2[OH:51])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCN(C(C)C)C(C)C.[C:67](Cl)(=[O:77])[C:68]1[CH:76]=[CH:75][C:71]([C:72](Cl)=[O:73])=[CH:70][CH:69]=1>CN1C(=O)CCC1>[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:51][C@@H:41]1[C@H:42]([OH:50])[C@@H:43]([NH:45][C:46](=[O:49])[CH2:47][CH3:48])[CH2:44][C@H:40]1[N:21]1[CH:20]=[N:19][C:18]2[C:22]1=[N:23][C:24]([N:26]1[CH2:30][CH2:29][C@@H:28]([NH:31][C:32](=[O:33])[NH:34][C@@H:35]3[CH2:39][CH2:38][N:37]([C:67]([C:68]4[CH:76]=[CH:75][C:71]([C:72]([OH:4])=[O:73])=[CH:70][CH:69]=4)=[O:77])[CH2:36]3)[CH2:27]1)=[N:25][C:17]=2[NH:16][CH2:15][CH:14]([C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7488Terephthaloyl chlorideHCID 81531DiisopropylethylamineHCID 66630460N-((1S,2R,3S,4R)-4-{6-(2,2-Diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate

Product 2

HCID 6422Trifluoroacetic acidHCID 866475524-[(R)-3-(3-{(R)-1-[9-((1R,2S,3R,4S)-2,3-Dihydroxy-4-propionylamino-cyclopentyl)-6-(2,2-diphenyl-ethylamino)-9H-purin-2-yl]-pyrrolidin-3-yl}-ureido)-pyrrolidine-1-carbonyl]-benzoic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

A solution of N-((1S,2R,3S,4R)-4-{6-(2,2-diphenyl-ethylamino)-2-[(R)-3-((R)-3-pyrrolidin-3-ylureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-propionamide trifluoroacetate (step 1) (0.02 g, 29 μmol) DIPEA (0.0075 g, 58 μmol) in NMP (0.2 ml) is treated with a solution of terephthaloyl chloride (0.006 g, 14.5 μmol) in NMP (0.1 ml). After stirring at room temperature for 1 hour the reaction mixture is purified by C-18 reverse phase column chromatography eluting with acetonitrile:water:TFA (0.1%) (gradient of 0 to 100% acetonitrile) to yield the title compound. (MH+ 831.6)

Workup

  1. customis purified by C-18 reverse phase column chromatography
  2. washeluting with acetonitrile

Sources & evidence

ORD record
ord-bcae611b605c451bbe93a3d6adfc1838
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

Loading…