Sodium Hydroxide → HCID 59166754, compound

HRID 1442959Notes

Reaction equation

HRID 1442959 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1.C[O:14][C:15]([C@@H:17]1[CH2:21][C@@H:20](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:19][N:18]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=O.[OH-].[Na+]>CCO>[CH3:3][CH2:2][O:1][C:15]([C@@H:17]1[CH2:21][C@H:20]([S:12][C:9]2[CH:10]=[CH:11][C:6]([Br:5])=[CH:7][CH:8]=2)[CH2:19][N:18]1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:14]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 660494-BromothiophenolHCID 2723922Sodium ethoxideHCID 134257721-tert-Butyl 2-methyl (2S,4R)-4-[(4-methylbenzene-1-sulfonyl)oxy]pyrrolidine-1,2-dicarboxylate

Product 1

HCID 59166754HCID 59166754, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium ethoxide (112 mg, 1.65 mmol) was added slowly to a stirred solution of 4-bromothiophenol (302 mg, 1.65 mmol) in EtOH (6 ml) at room temperature under a nitrogen atmosphere. A solution of (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (CAS Reg. No. 88043-21-4) (300 mg, 0.75 mmol) in 1 ml EtOH was added after 30 minutes and the solution was stirred for 48 h. The reaction mixture was poured into 0.5M NaOH (50 ml) and extracted with CH2Cl2 (2×50 ml). The combined organics were dried (magnesium sulphate) and concentrated under vacuum. Flash column chromatography yielded the product as a pink solid (120 mg, 40%).

Workup

  1. extractionextracted with CH2Cl2 (2×50 ml)
  2. dry with materialThe combined organics were dried (magnesium sulphate)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6e2b32262c3e43a0b45f9761aa6fbe3f
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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