Hydrochloric Acid → N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanine

HRID 1016243Notes

Reaction equation

HRID 1016243 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].O1CCOCC1.[C:13](ON1C(=O)CCC1=O)([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14].Cl>O.C(=O)([O-])[O-].[Na+].[Na+]>[C:13]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])([O:15][CH2:16][CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:24]2[C:29]1=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 312751,4-DioxaneHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Product 1

HCID 6364642N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 10340Sodium CarbonateSolvent2×

Procedure

1 g of each isotope labeled alanine (11.2 mmol) were dissolved in 15 mL of purified water and 1.2 g of sodium carbonate (see Figure GP2). 15 mL of 1,4-Dioxane was added slowly to each and stirred. Over the period of two and a half hours, 3.8 g of Fmoc-OSu (9-Fluorenylmethyl-N-hydroxysuccinimide) was added to each (see Figure GP3 for scheme). Additional saturated sodium carbonate in water was added to maintain a pH=10. Solutions were allowed to stir overnight. 6M HCl was slowly added to the solution until the pH was approximately 2. Extraction of the compound was completed using two times 150 mL of ethyl acetate, washing four times with 300 mL of acidified/purified water. Magnesium sulfate was added to remove any excess water. Samples were filtered and concentrated using a RotoVap until the final volume was approximately one-third the original volume. Crystallization was completed using Hexane. Hexane was decanted and compound allowed to dry.

Workup

  1. temperatureto maintain a pH=10
  2. stirringto stir overnight
  3. extractionExtraction of the compound
  4. washwashing four times with 300 mL of acidified/purified water
  5. additionMagnesium sulfate was added
  6. customto remove any excess water
  7. filtrationSamples were filtered
  8. concentrationconcentrated
  9. customCrystallization
  10. customHexane was decanted
  11. customto dry

Sources & evidence

ORD record
ord-8f8eb9b6540e4e1da3c5263e3adb1be9
Source dataset
uspto-grants-2002_11
Patent number
US06475807B1

Reaction notes

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