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L-Phenylalanine → Fmoc-phenylalanine

HRID 1089820
Notes
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Reaction equation

HRID 1089820 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13](=[O:16])([O-])[O-:14].[Na+].[Na+].C(=O)([O-])ON1C(=O)CC([CH2:27][CH:28]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:34]3[C:29]2=[CH:30][CH:31]=[CH:32][CH:33]=3)C1=O>O.O1CCOCC1>[CH:30]1[C:29]2[CH:28]([CH2:27][O:14][C:13]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:16])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6140L-PhenylalanineHCID 10340Sodium CarbonateHCID 71304114(9H-fluoren-9-yl)methyl-2,5-dioxopyrrolidin-1-yl carbonate

Product 1

HCID 978331Fmoc-phenylalanineYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 31275
1,4-Dioxane
Solvent

Procedure

Phenylalanine (27.25 g, 0.165 mole) was dissolved in a solution of sodium carbonate (31.8 g, 0.3 mole) in 320 ml of water. This mixture was added to a solution of 9-fluorenylmethylsuccinimidyl carbonate (50.8 g, 0.15 mole) dissolved in a minimum amount of dioxane (approximately 90 ml being required). The mixture was stirred vigorously (mechanical stirring) at room temperature for 22 hours and then diluted with water. The reaction mixture was extracted twice with ethyl ether and then acidified to pH 2 with concentrated hydrochloric acid in the presence of 750 ml of ethyl acetate. The organic layer was separated, washed twice with 1 N hydrochloric acid, twice with water, once with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The product was crystallized by addition of hexane to the boiling ethyl acetate solution, to give 18 g of N-[(9H-fluoren-9ylmethyloxy)carbonyl]-L-phenylalanine, mp 179°-181° C.

Workup

  1. stirring(mechanical stirring) at room temperature for 22 hours
  2. extractionThe reaction mixture was extracted twice with ethyl ether
  3. customThe organic layer was separated
  4. washwashed twice with 1 N hydrochloric acid, twice with water, once with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe product was crystallized by addition of hexane to the boiling ethyl acetate solution

Sources & evidence

ORD record
ord-8ae7059f257b43f88840e4a563571435
Source dataset
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05079260

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes