Hydrochloric Acid → HCID 11773132, compound

HRID 1061475Notes

Reaction equation

HRID 1061475 reaction equation
[C:1]1([CH3:11])[CH:6]=CC(S(Cl)(=O)=O)=C[CH:2]=1.Cl.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1.[OH2:24].[C:25]([O-:28])(O)=[O:26].[Na+].[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[OH:24][CH2:31][C@@H:32]1[CH2:33][C@@H:34]([O:21][S:20]([C:17]2[CH:16]=[CH:15][C:14]([CH3:13])=[CH:19][CH:18]=2)(=[O:23])=[O:22])[CH2:35][N:30]1[C:25]([O:28][C:1]([CH3:11])([CH3:6])[CH3:2])=[O:26]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 11773132HCID 11773132, compound

Procedure

2a(2) (3.41 g, 10.3 mmol) was dissolved in anhydrous pyridine (30.0 mL) and cooled to 0° C. p-Toluenesulfonylchloride (5.89 g, 30.9 mmol) was then added in portions over a 10 minute period. The flask was then placed in a refrigerator at 4° C. for 48 h. The resulting solution was poured into 1 N HCl (300 mL), extracted with methylene chloride (3×200 mL) and the organics were dried over anhydrous sodium sulfate. The crude tosylate intermediate was dissolved in THF (50 mL), to which was added H2O (0.5 mL) followed by pTSA-H2O (1.03 mmol). Once the reaction was complete as determined by TLC, the mixture was poured into saturated aqueous NaHCO3 (150 mL) and extracted with methylene chloride (3×50 mL). The combined organics were dried over sodium sulfate. The crude alcohol was purified by flash chromatography on SiO2 eluting with acetone/chloroform (0-5-10% acetone) to give 2.71 g (71% for 2-steps) of (2S-trans)-2-hydroxymethyl-4-[[(4-methylphenyl)sulfonyl]oxy]-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester (2a(3)) as a clear oil:

Workup

  1. additionwas then added in portions over a 10 minute period
  2. extractionextracted with methylene chloride (3×200 mL)
  3. dry with materialthe organics were dried over anhydrous sodium sulfate
  4. dissolutionThe crude tosylate intermediate was dissolved in THF (50 mL), to which
  5. additionwas added H2O (0.5 mL)
  6. extractionextracted with methylene chloride (3×50 mL)
  7. dry with materialThe combined organics were dried over sodium sulfate
  8. customThe crude alcohol was purified by flash chromatography on SiO2 eluting with acetone/chloroform (0-5-10% acetone)

Sources & evidence

ORD record
ord-6e461851a11c4cc9a28432abef5af3dc
Source dataset
uspto-grants-2005_11
Patent number
US06960474B2

Reaction notes

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