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Sodium Carbonate → Fmoc-Gly-Pro-Hyp

HRID 1748
Notes
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Reaction equation

HRID 1748 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH2:20][CH2:19][CH2:18][C@H:6]1[C:7]([N:9]1[CH2:17][C@H:15]([OH:16])[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])=[O:4].[C:21](=O)([O:37]N1C(=O)CCC1=O)[O:22][CH2:23][CH:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2.C([O-])([O-])=O.[Na+].[Na+]>C([O-])([O-])=O.[Na+].[Na+].O.C(COC)OC>[NH:1]([C:21]([O:22][CH2:23][CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]2[C:36]1=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:37])[CH2:2][C:3]([N:5]1[CH2:20][CH2:19][CH2:18][C@H:6]1[C:7]([N:9]1[CH2:17][C@H:15]([OH:16])[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 11778669Glycyl-prolyl-hydroxyproline2×

Product 1

HCID 95565904Fmoc-Gly-Pro-Hyp

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolvent2×
HCID 2735133
Sodium Carbonate Monohydrate
Solvent

Conditions

Temperature
4 °C

Procedure

Fmoc-Gly-Pro-Hyp was synthesized from Gly-Pro-Hyp as follows: 3.0 g Gly-Pro-Hyp (10.5 mmol) was dissolved in 54 mL Na2CO3 --H2O (1:9) and stored at 4° C. 4.05 g 9-fluorenylmethyl succinimidyl carbonate (12.0 mmol) was dissolved in 45 mL dimethoxyethane and stirred at 4° C. The aqueous Na2CO3 solution was added slowly to the dimethoxyethane solution, and the reaction proceeded for 2.5 h at 4° C. and 21 h at room temperature. The solution was filtered, and 360 mL H2O was added to the filtrate. The aqueous layer was extracted with 300 mL of diethyl ether, acidified to pH 2 with concentrated HCl, reduced to half volume at 80° C. under reduced pressure, and stored at 4° C. for 24 h. The aqueous layer was decanted from the oily precipitate, reduced to ~30 mL at 81° C. under reduced pressure, and stored at 4° C. for 24 h. The aqueous layer was decanted from the oily precipitate. Both oily precipitates were dissolved in a total of 20 mL methanol, then 250 mL ethyl acetate was added. A white residue was recovered by evaporation at 73° C. for 1 h under reduced pressure; yield 3.23 g (6.39 mmol, 60.6%). The identity of the product as Fmoc-Gly-Pro-Hyp and its homogeneity was verified by thin layer chromatography [chloroform-methanol-HOAc (95:20:3)], scanning UV spectroscopy, and Edman degradation sequence analysis.

Workup

  1. customstored at 4° C
  2. filtrationThe solution was filtered
  3. addition360 mL H2O was added to the filtrate
  4. extractionThe aqueous layer was extracted with 300 mL of diethyl ether
  5. customreduced to half volume at 80° C. under reduced pressure
  6. waitstored at 4° C. for 24 h
  7. customThe aqueous layer was decanted from the oily precipitate
  8. customreduced to ~30 mL at 81° C. under reduced pressure
  9. waitstored at 4° C. for 24 h
  10. customThe aqueous layer was decanted from the oily precipitate
  11. customBoth oily precipitates
  12. dissolutionwere dissolved in a total of 20 mL methanol
  13. addition250 mL ethyl acetate was added
  14. customA white residue was recovered by evaporation at 73° C. for 1 h under reduced pressure

Sources & evidence

ORD record
ord-0d0cde9f744f4003bee69dc9e97ec82e
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726243

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes