Hydrochloric Acid → HCID 15671503, compound

HRID 1088277Notes

Reaction equation

HRID 1088277 reaction equation
[N+:1]([C:4]1[CH:36]=[CH:35][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][Si](C(C)(C)C)(C)C)[CH2:14][C@H:13]2[CH2:25][CH:26](C(OC)=O)[C:27]([O:29]C)=[O:28])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O.O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]2[CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:11])=[CH:35][CH:36]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 15671501HCID 15671501, compound

Product 1

HCID 15671503HCID 15671503, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2R,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-(2,2-dimethoxycarbonylethyl)-4-t-butyldimethylsilyloxypyrrolidine (1.04 g) was dissolved in 6 ml of methanol, 3 ml of 4N sodium hydroxide solution was added thereto, and the resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was acidified with 6 ml of 6N hydrochloric acid, and 5 ml of tetrahydrofuran was added thereto. The resulting mixture was stirred at room temperature for 2 days, diluted with water, adjusted to alkaline with a saturated sodium bicarbonate solution and extracted with ether. The aqueous layer was acidified (pH 1) with dilute hydrochloric acid, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and distilled to obtain (2R,4R)-1-(p-nitrobenzyloxycarbonyl)-2-(2-carboxyethyl)-4-hydroxypyrrolidine.

Workup

  1. additionwas added
  2. stirringThe resulting mixture was stirred at room temperature for 2 days
  3. extractionextracted with ether
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled

Sources & evidence

ORD record
ord-d6e8ef938319424eb2401bfd10765d45
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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