Ammonium Chloride → HCID 53845871, compound

HRID 1657249Notes

Reaction equation

HRID 1657249 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]1([CH2:14][C@H:15]2[C@H:19]([C:20](OC)=[O:21])[O:18][C:17]([CH3:25])([CH3:24])[N:16]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[Cl-].[NH4+]>CCOCC>[C:20]([C@@H:19]1[O:18][C:17]([CH3:24])([CH3:25])[N:16]([C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[C@H:15]1[CH2:14][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)(=[O:21])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86747329HCID 86747329, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 53845871HCID 53845871, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2.36 ml (2 mmol) of a 0.76N solution of phenyllithium in ether are sprayed at -75° into 355 mg (1 mmol) of 3-t-butyl 5-methyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-3,5-oxazolidinedicarboxylate in 20 ml of ether and the reaction mixture is stirred at this temperature for 30 minutes, subsequently poured into 50 ml of saturated ammonium chloride solution and extracted three times with 150 ml of ether each time. The three ether extracts are washed in succession with in each case 70 ml of 2N sodium bicarbonate solution and 70 ml of saturated sodium chloride solution, combined, dried over magnesium sulphate, filtered and evaporated. The residual oil (540 mg) is chromatographed on 30 g of silica gel with a 98:2 mixture of toluene and ethyl acetate as the eluting agent, whereby there are obtained 300 mg of t-butyl (4S,5R)-5-benzoyl-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a white solid, MS: 401 (M)+.

Workup

  1. extractionextracted three times with 150 ml of ether each time
  2. washThe three ether extracts are washed in succession with in each case 70 ml of 2N sodium bicarbonate solution and 70 ml of saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residual oil (540 mg) is chromatographed on 30 g of silica gel with a 98:2 mixture of toluene and ethyl acetate as the eluting agent, whereby there

Sources & evidence

ORD record
ord-f384137468b64cc696e0de28fa4f540d
Source dataset
uspto-grants-1993_10
Patent number
US05256645

Reaction notes

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