Benzenesulfonamide → n-(2-Hydroxy-indan-1-yl)-2-[4-(6-methoxy-3-phenyl-naphthalen-1-yloxy)-2-(1-phenylmethanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-pyrrolidin-1-yl]-3,3-dimethyl-butyramide

HRID 1822434Notes

Reaction equation

HRID 1822434 reaction equation
[OH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[NH:11][C:12]([CH:14]([N:19]1[CH2:23][CH:22]([O:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=3)[CH:28]=[C:27]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:26]=2)[CH2:21][CH:20]1[C:43]1([C:48](O)=[O:49])[CH2:45][CH:44]1[CH:46]=[CH2:47])[C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[C:51]1([S:57]([NH2:60])(=[O:59])=[O:58])C=CC=CC=1.C(N([CH:67]([CH3:69])[CH3:68])CC)(C)C.[CH2:70]1[CH2:74]N([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)C[CH2:71]1.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[OH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[NH:11][C:12](=[O:13])[CH:14]([N:19]1[CH2:23][CH:22]([O:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=3)[CH:28]=[C:27]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:26]=2)[CH2:21][CH:20]1[C:43]1([C:48]([NH:60][S:57]([CH2:51][C:68]2[CH:67]=[CH:69][CH:74]=[CH:70][CH:71]=2)(=[O:59])=[O:58])=[O:49])[CH2:45][CH:44]1[CH:46]=[CH2:47])[C:15]([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 5

HCID 7370BenzenesulfonamideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 68493461HCID 68493461, compound

Product 1

HCID 68493430n-(2-Hydroxy-indan-1-yl)-2-[4-(6-methoxy-3-phenyl-naphthalen-1-yloxy)-2-(1-phenylmethanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-pyrrolidin-1-yl]-3,3-dimethyl-butyramide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To solution of 14 (25 mg, 0.033 mmol) in chloroform (1 mL) was added benzenesulfonamide (10.5 mg, 0.066 mmol) followed by diisopropylethylamine (34 μL, 0.197 mmol). The solution was stirred at RT for 10 min and then at −20° C. for 30 min. PyBOP (76 mg, 0.13 mmol) was then added as a solid. The solution was kept at −20° C. for 48 hours. The solution was then poured into aqueous NaHCO3 (sat.) and washed with water. The organic layer was dried, concentrated and subjected to purification by HPLC, affording the title compound as a white solid.

Workup

  1. waitat −20° C. for 30 min
  2. waitThe solution was kept at −20° C. for 48 hours
  3. washwashed with water
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customsubjected to purification by HPLC

Sources & evidence

ORD record
ord-ec00197691184e7fbdb8f315c7ccf945
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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