N-Benzenesulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid, methyl ester → N-Benzenesulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid

HRID 1070440Notes

Reaction equation

HRID 1070440 reaction equation
[C:1]1([S:7]([N:10]2[CH2:28][CH2:27][CH2:26][C@H:11]2[C:12]([C:14]23[CH2:20][CH:17]([CH2:18][CH2:19]2)[CH2:16][C:15]3([NH2:25])[C:21]([O:23]C)=[O:22])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[OH-].[Na+].CO>[C:1]1([S:7]([N:10]2[CH2:28][CH2:27][CH2:26][C@H:11]2[C:12]([C:14]23[CH2:20][CH:17]([CH2:18][CH2:19]2)[CH2:16][C:15]3([NH2:25])[C:21]([OH:23])=[O:22])=[O:13])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86759758N-Benzenesulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid, methyl ester

Product 1

HCID 69755327N-Benzenesulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-phenylsulfonyl-(L)-prolyl-2-amino-2-norbornanecarboxylic acid, methyl ester (210 mg, 0.2 mmol) in 3 mL of 1:1 aqueous sodium hydroxide (1 M) and methanol was stirred at room temperature for 2 weeks. The reaction was quenched with concentrated hydrochloric acid (0.2 mL), and the resulting mixture was partitioned between saturated salt solution and ethyl acetate. The product was extracted with ethyl acetate and was purified by flash chromatography on silica gel eluted with 100:5:1 methylene chloride/methanol/acetic acid to give the product as a mixture of diastereomers.

Workup

  1. customThe reaction was quenched with concentrated hydrochloric acid (0.2 mL)
  2. customthe resulting mixture was partitioned between saturated salt solution and ethyl acetate
  3. extractionThe product was extracted with ethyl acetate
  4. customwas purified by flash chromatography on silica gel
  5. washeluted with 100:5:1 methylene chloride/methanol/acetic acid
  6. customto give the product
  7. additionas a mixture of diastereomers

Sources & evidence

ORD record
ord-24401f6812054bc092cb8b47e84cd0b8
Source dataset
uspto-grants-2005_06
Patent number
US06903075B1

Reaction notes

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