Citric Acid → HCID 59608394, compound

HRID 2069158Notes

Reaction equation

HRID 2069158 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[C:13](=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[C:28](O)(=O)[CH2:29][C:30]([CH2:35][C:36](O)=O)(C(O)=O)O>O1CCOCC1.O.O>[CH3:25][C:24]([CH3:27])([O:23][C:21](=[O:22])[CH2:20][NH:12][C@@H:8]([C:9]([OH:11])=[O:10])[CH:7]([C:28]1[CH:29]=[CH:30][CH:35]=[CH:36][CH:13]=1)[C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH3:26]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 71567D-PhenylalanineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 59608394HCID 59608394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a stirred mixture of D-diphenylalanine, H-D-Dpa-OH, (20.0 g, 82.9 mmol) and potassium carbonate (17.2 g, 125 mmol) in dioxane/water (1:1 (v/v), 100 ml) was added tert-butyl bromoacetate (12.2 ml, 83.0 mmol). After stirring overnight water (100 ml) was added and the pH adjusted to 5.5 with 0.5M citric acid solution. The resultant precipitate was filtered off, washed with water then diethyl ether and dried under vacuum to give 10.4 g of the title compound a.

Workup

  1. additionwas added
  2. filtrationThe resultant precipitate was filtered off
  3. washwashed with water
  4. dry with materialdiethyl ether and dried under vacuum

Sources & evidence

ORD record
ord-44b8820ce3334799afe685d1009c4203
Source dataset
uspto-grants-2012_10
Patent number
US08299091B2

Reaction notes

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