O-Phenylenediamine → tert-butyl (1S)-2-[(2-aminophenyl)amino]-1-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl]-2-oxoethylcarbamate

HRID 724706Notes

Reaction equation

HRID 724706 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[S:24](=[O:26])(=[O:25])[N:23]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:22](=[O:31])[CH2:21]2)=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:65]1([NH2:72])[C:66]([NH2:71])=[CH:67][CH:68]=[CH:69][CH:70]=1>CN(C)C=O>[NH2:71][C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][C:65]=1[NH:72][C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[S:24](=[O:26])(=[O:25])[N:23]([C:27]([CH3:29])([CH3:28])[CH3:30])[C:22](=[O:31])[CH2:21]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11568707(2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid

Product 1

HCID 58746687tert-butyl (1S)-2-[(2-aminophenyl)amino]-1-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)benzyl]-2-oxoethylcarbamateYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N,N-dimethylformamide (5.0 mL) was added (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid (709.6 mg, 1.561 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (712 mg, 1.87 mmol), and N,N-diisopropylethylamine (1.3 mL, 7.80 mmol) and premixed for 5 minutes and then 1,2-benzenediamine (253 mg, 2.34 mmol) was added and stirred at room temperature overnight. Product was concentrated and purified on preparative LCMS to give the product (690 mg, 67%). LCMS found for C27H37N4O6S (M+H)+: m/z=545.

Workup

  1. additionpremixed for 5 minutes
  2. concentrationProduct was concentrated
  3. custompurified on preparative LCMS

Sources & evidence

ORD record
ord-2d063570e2f7444b9b5a2c3a9281e5b6
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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