Sodium Hydroxide → n-(n-(3-Methyl-benzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(n-(3,5-dichloroisonicotinoyl)-amino)-(l)-phenylalanine

HRID 23886Notes

Reaction equation

HRID 23886 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:19][CH:18]3[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH:12]2[C:20]([NH:22][C@H:23]([C:42]([O:44]C)=[O:43])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:41])[C:33]3[C:38]([Cl:39])=[CH:37][N:36]=[CH:35][C:34]=3[Cl:40])=[CH:27][CH:26]=2)=[O:21])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:19][CH:18]3[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH:12]2[C:20]([NH:22][C@H:23]([C:42]([OH:44])=[O:43])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:41])[C:33]3[C:38]([Cl:39])=[CH:37][N:36]=[CH:35][C:34]=3[Cl:40])=[CH:29][CH:30]=2)=[O:21])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131724738N-(N-(3-methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester

Product 1

HCID 20758782n-(n-(3-Methyl-benzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(n-(3,5-dichloroisonicotinoyl)-amino)-(l)-phenylalanineYield 75.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-(N-(3-Methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)amino)-(L)-phenylalanine, methyl ester (0.036 mmol, 24 mg) was dissolved 0.089 mL of MeOH and 0.089 mL of a 0.4 N solution of NaOH in MeOH. The resulting mixture was stirred overnight at rt. Volatiles were removed in vacuo and the residue was partitioned between 5% citric acid and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (2×). The organic extracts were combined and washed with brine, and dried over anhydrous Na2SO4. The residue obtained after filtration and evaporation of volatiles was purified by flash column chromatography on silica gel eluted with a mixture of CH2Cl2 and MeOH to provide N-(N-(3-methylbenzenesulfonyl)-octahydroisoindole-1-carbonyl)-4-(N-(3,5-dichloroisonicotinoyl)-amino)-(L)-phenylalanine (18 mg, 67%) as a white foam (homogeneous by TLC (9:1 dichloromethane: methanol)).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue was partitioned between 5% citric acid and CH2Cl2
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe residue obtained
  7. filtrationafter filtration and evaporation of volatiles
  8. customwas purified by flash column chromatography on silica gel
  9. washeluted with a mixture of CH2Cl2 and MeOH

Sources & evidence

ORD record
ord-0fd5c2235bf4493f88a4600e3ed4abf8
Source dataset
uspto-grants-2005_02
Patent number
US06855708B2

Reaction notes

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