Citric Acid → HCID 57237021, compound

HRID 1078709Notes

Reaction equation

HRID 1078709 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32][CH:33]([NH:38][C:39]([O:41][CH2:42][CH:43]=[CH2:44])=[O:40])[C:34](OC)=[O:35])=[O:6])[CH:2]=[CH2:3].[Cl-].[Li+].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][C@H:8]1[CH2:32][CH:33]([NH:38][C:39]([O:41][CH2:42][CH:43]=[CH2:44])=[O:40])[CH2:34][OH:35])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 57142708HCID 57142708, compound

Product 1

HCID 57237021HCID 57237021, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,4S)-N-allyloxycarbonyl-2-(2-allyloxycarbonylamino-2-methoxycarbonylethyl)-4-(triphenylmethylthio)pyrrolidine prepared in REFERENCE EXAMPLE 2-2 (810 mg, 1.32 mmol) in tetrahydrofuran (5 ml) was added lithium chloride (100 mg, 2.58 mmol), sodium borohydride (110 mg, 2.59 mmol) and ethanol (5 ml) under a nitrogen atmosphere, and the mixture was stirred overnight at room temperature. The reaction mixture was acidified with 10% aqueous citric acid under ice-cooling, and then the organic solvent was removed in vacuo. The residual aqueous solution was extracted with methylene chloride (1×40 ml, 2×20 ml), and the combined organic layer was washed successively with water and saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the solvent was removed in vacuo, and the residue was subjected to silica gel column chromatography (heptane-ethyl acetate) to give (2R,4S)-N-allyloxycarbonyl-2-(2-allyloxycarbonylamino-3-hydroxypropyl)-4-(triphenylmethylthio)pyrrolidine (440 mg, yield: 57%).

Workup

  1. temperaturecooling
  2. customthe organic solvent was removed in vacuo
  3. extractionThe residual aqueous solution was extracted with methylene chloride (1×40 ml, 2×20 ml)
  4. washthe combined organic layer was washed successively with water and saturated aqueous sodium chloride
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4959a5096bcb41c7bf4c3785857d2dee
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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