Citric Acid → HCID 10349045, compound

HRID 258171Notes

Reaction equation

HRID 258171 reaction equation
[C:1]([O:5][P:6]([C:13]([F:28])([F:27])[C:14]1[CH:26]=[CH:25][C:17]([CH2:18][CH:19]([C:21](OC)=[O:22])[NH2:20])=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH:31]1[CH:36]=[C:35]2[CH:37]([CH2:44][O:45][C:46](ON3N=NC4C3=CC=CC=4)=[O:47])[C:38]3[C:43]([C:34]2=[CH:33][CH:32]=1)=[CH:42][CH:41]=[CH:40][CH:39]=3.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:61]>O1CCOCC1>[C:9]([O:8][P:6]([C:13]([F:28])([F:27])[C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH:19]([C:21]([OH:61])=[O:22])[NH:20][C:46]([O:45][CH2:44][CH:37]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:43]=3[C:34]3[C:35]2=[CH:36][CH:31]=[CH:32][CH:33]=3)=[O:47])=[CH:25][CH:26]=1)([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 5236567Fmoc-OBtHCID 10454855HCID 10454855, compound

Product 1

HCID 10349045HCID 10349045, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of amino ester 12 (15 mg, 0.036 mmol) in dioxane (0.5 mL) is added 1 N NaOH (0.18 mL) and the reaction is stirred at ambient temperature. After 20 minutes CO2 gas is bubbled into the reaction for 5 minutes, then solid Fmoc-OBt (15 mg, 0.043 mmol) is added and stirring continued for 1 hour. Cold 5% citric acid (10 mL) is added and the mixture is extracted with CHCl' (3×10 mL); the combined extracts are dried (MgSO4) and the solvent evaporated in vacuo to yield crude 14 (13.7 mg, 60%).

Workup

  1. customAfter 20 minutes CO2 gas is bubbled into the reaction for 5 minutes
  2. stirringstirring
  3. extractionthe mixture is extracted with CHCl' (3×10 mL)
  4. dry with materialthe combined extracts are dried (MgSO4)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-105a33cf345d4527ae90bdc07e36d850
Source dataset
uspto-grants-1993_11
Patent number
US05264607

Reaction notes

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