Triphenylphosphine → (2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoate

HRID 340505Notes

Reaction equation

HRID 340505 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O-:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:46]([O:50][C:51](=[O:60])[NH:52][C@H:53]([CH:55](O)[CH2:56][CH2:57][CH3:58])[CH3:54])([CH3:49])([CH3:48])[CH3:47]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH:55]([CH2:56][CH2:57][CH3:58])[C@@H:53]([NH:52][C:51]([O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:60])[CH3:54])=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 44199404-NitrobenzoateHCID 87514848tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate

Product 1

HCID 86683881(2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoateYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-nitrobenzoate (16.3 g), triphenylphosphine (32 g), and diisopropyl azodicarboxylate (40% toluene solution) (64 ml) were added dropwise to a tetrahydrofuran (50 ml) solution containing tert-butyl((2S)-3-hydroxyhexan-2-yl)carbamate (17 g) for 30 minutes, followed by stirring at room temperature for 14 hours. The solvent was distilled away from the reaction solution under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5.5:1), and a yellow solid of (2S)-2-((tert-butoxycarbonyl)amino)hexane-3-yl 4-nitrobenzoate (17 g) was thus obtained.

Workup

  1. distillationThe solvent was distilled away from the reaction solution under reduced pressure
  2. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5.5:1)

Sources & evidence

ORD record
ord-44aa852be7c1423898b3a2ff746c57a8
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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