Phthalimide → HCID 54458704, compound

HRID 847318Notes

Reaction equation

HRID 847318 reaction equation
[CH:1]1([CH2:7][CH:8]2[CH:12]([CH2:13][CH:14]([CH:18]([CH3:20])[CH3:19])[CH2:15][CH2:16]O)[O:11][C:10]([CH3:22])([CH3:21])[N:9]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49]1(=[O:59])[NH:53][C:52](=[O:54])[C:51]2=[CH:55][CH:56]=[CH:57][CH:58]=[C:50]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]1([CH2:7][C@H:8]2[C@H:12]([CH2:13][C@@H:14]([CH:18]([CH3:20])[CH3:19])[CH2:15][CH2:16][N:53]3[C:49](=[O:59])[C:50]4=[CH:58][CH:57]=[CH:56][CH:55]=[C:51]4[C:52]3=[O:54])[O:11][C:10]([CH3:21])([CH3:22])[N:9]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19882234HCID 19882234, compound

Product 1

HCID 54458704HCID 54458704, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.0 g (12.15 mmol) of t-butyl 4-(cyclohexylmethyl)-5-(4-hydroxy-2-isopropylbutyl)-2,2-dimethyl-3-oxazolidinecarboxylate, 4.68 g (17.8 mmol) of triphenylphosphine and 2.48 g (17 mmol) of phthalimide are dissolved in 70 ml of tetrahydrofuran and cooled to 10°. Then, a solution of 2.8 ml (17.8 mmol) of diethyl azodicarboxylate in 15 ml of tetrahydrofuran is added dropwise within 10 minutes and the reaction mixture is stirred at room temperature for 4 hours. Then, the reaction mixture is evaporated under reduced pressure and the residue is chromatographed on 160 g of silica gel with a mixture of methylene chloride and hexane as the eluting agent, whereby there are obtained 5.4 g of t-butyl (4S,5S)-4-(cyclohexylmethyl)-5-[(S)-2-isopropyl-4-phthalimidobutyl]-2,2-dimethyl-3-oxazolidinecarboxylate as an oil, MS: 525 (M-CH3)+.

Workup

  1. temperaturecooled to 10°
  2. customThen, the reaction mixture is evaporated under reduced pressure
  3. customthe residue is chromatographed on 160 g of silica gel with a mixture of methylene chloride and hexane as the eluting agent, whereby there

Sources & evidence

ORD record
ord-3af284527ba349c8ac31d7c4d39e2221
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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