L-Hydroxyproline → (2S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

HRID 977510Notes

Reaction equation

HRID 977510 reaction equation
[C:1](Cl)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[OH:19][C@H:20]1[CH2:24][NH:23][C@H:22]([C:25]([OH:27])=[O:26])[CH2:21]1>C(Cl)Cl>[C:1]([N:23]1[CH2:24][C@H:20]([OH:19])[CH2:21][C@H:22]1[C:25]([OH:27])=[O:26])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Participants

4

Reactant 2

HCID 5810L-HydroxyprolineHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 2756109(2S,4R)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The FMOC-trans-4-hydroxy-L-proline 57 was prepared as follows: 1.1 equivalents of FMOC-chloride is added to 1.0 equivalents of trans-4-hydroxy-L-proline (Aldrich company) and allowed to stir for 12 hour at 25° C. in 0.10M methylene chloride. The resulting mixture is quenched with water, washed with sodium bicarbonate and dried over magnesium sulfate (standard workup conditions). The crude compound can then be purified by flash chromatography. Mass Spectral analysis: m/e calc'd for C53H58O11N2Cs (M+Cs+): 1031.3095, found 1031.3143

Workup

  1. customThe resulting mixture is quenched with water
  2. washwashed with sodium bicarbonate
  3. dry with materialdried over magnesium sulfate (standard workup conditions)
  4. customThe crude compound can then be purified by flash chromatography

Sources & evidence

ORD record
ord-03a227a260764df88593281a71028907
Source dataset
uspto-grants-1997_03
Patent number
US05614615

Reaction notes

Loading…