Sodium Hydroxide → HCID 68461007, compound

HRID 501488Notes

Reaction equation

HRID 501488 reaction equation
[NH:1]1[CH:5]([C:6]([OH:8])=[O:7])[CH2:4][CH:3]2[CH2:9][CH2:10][CH2:11][CH:2]12.[OH-].[Na+].[C:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)(=[O:16])[CH3:15]>CN(C=O)C>[C:14]([C:17]1[CH:18]=[CH:19][C:20]([S:23]([N:1]2[CH:5]([C:6]([OH:8])=[O:7])[CH2:4][CH:3]3[CH2:9][CH2:10][CH2:11][CH:2]23)(=[O:25])=[O:24])=[CH:21][CH:22]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 11446836HCID 11446836, compound

Product 1

HCID 68461007HCID 68461007, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

1 g of octahydrocyclopenta[b]pyrrole-2-carboxylic acid (6.45 mmol) was dissolved in 20 ml of DMF, after which 3 equivalents of a 3N solution of NaOH (6.45 ml) were added at 0° C. After 10 min, a solution of 1.55 g of 4-acetylbenzenesulfonyl chloride (1.1 equivalents, 7.1 mmol) in 8 ml of DMF was slowly added dropwise; after it had reached RT, the mixture was stirred at 40° C. for a further 6 h and, after that, the solvent was removed under reduced pressure. The crude product was purified chromatographically.

Workup

  1. customhad reached RT
  2. customafter that, the solvent was removed under reduced pressure
  3. customThe crude product was purified chromatographically

Sources & evidence

ORD record
ord-a2929bb4f7b84e409ba16a1012676e2c
Source dataset
uspto-grants-2010_08
Patent number
US07772270B2

Reaction notes

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