N-(9-Fluorenylmethoxycarbonyloxy)succinimide → Fmoc-L-Prolinol

HRID 2361732Notes

Reaction equation

HRID 2361732 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:2]1[CH2:3][OH:4].[CH:8]1[C:20]2[CH:19]([CH2:21][O:22][C:23](ON3C(=O)CCC3=O)=[O:24])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]=[CH:10][CH:9]=1>O.C1COCC1>[C:23]([N:1]1[CH2:7][CH2:6][CH2:5][C@H:2]1[CH2:3][OH:4])([O:22][CH2:21][CH:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2[C:20]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:24]

Participants

5

Reactant 2

HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide2×HCID 640091L-Prolinol5×

Product 1

HCID 688635Fmoc-L-ProlinolYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

L-prolinol (Compound 1) (0.61 g, 6.0 mmol) was dissolved in 70 ml of pure water, thus preparing an L-prolinol aqueous solution. N-(9-Fluorenylmethoxycarbonyloxy)succinimide (Fmoc-OSu) (2.0 g, 6.0 mmol) was dissolved in 10 ml of THF. This THF solution was added to the L-prolinol aqueous solution, and this was stirred for 1 hour so as to react the L-prolinol and the Fmoc-OSu. The reaction solution was separated into a liquid fraction and a precipitate fraction. These fractions respectively were subjected to extraction with ethyl acetate, and organic layers respectively were collected therefrom. The thus-obtained organic layers were mixed together, and anhydrous sodium sulfate was added thereto to absorb moisture (hereinafter, this process is referred to as a “drying” process). The organic layers were filtered, and the filtrate obtained was vacuum concentrated. The residual substance obtained was purified by silica gel column chromatography (the eluent hexane:ethyl acetate=1:1). Thus, Compound 2 was obtained (1.4 g, yield: 74%). The result of NMR analysis with respect to this compound is shown below.

Workup

  1. customThe reaction solution was separated into a liquid fraction
  2. extractionThese fractions respectively were subjected to extraction with ethyl acetate, and organic layers
  3. customrespectively were collected
  4. additionThe thus-obtained organic layers were mixed together
  5. additionanhydrous sodium sulfate was added
  6. customto absorb moisture (hereinafter, this process
  7. customdrying” process)
  8. filtrationThe organic layers were filtered
  9. customthe filtrate obtained
  10. concentrationconcentrated
  11. customThe residual substance obtained
  12. customwas purified by silica gel column chromatography (the eluent hexane

Sources & evidence

ORD record
ord-11654023fca94d49b679868761aa4c2f
Source dataset
uspto-grants-2014_04
Patent number
US08691782B2

Reaction notes

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