Citric Acid → HCID 131715723, compound

HRID 623276Notes

Reaction equation

HRID 623276 reaction equation
S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@H:13]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:14]([CH2:16][CH3:17])[CH3:15].[NH:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:29]([C:31](O)=[O:32])[CH3:30].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CCOC(C)=O.CCN(CC)CC>[NH:28]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C@H:29]([C:31]([NH:12][C@H:13]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:14]([CH2:16][CH3:17])[CH3:15])=[O:32])[CH3:30]

Participants

9

Reactant 6

HCID 311Citric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanineHCID 85570p-ToluenesulfonateHCID 7350013HCID 7350013, compound

Product 1

HCID 131715723HCID 131715723, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

23.61 g of tosylate of H-Ile-OBzl and 11.35 g of Boc-Ala-OH are suspended in 500 ml of AcOEt. To this mixture 6.07 g of Et3N and 8.92 g of HOBt and then 12.65 g of WSC are added with cooling in an ice bath. Stirring is continued whilst cooling the reaction mixture in an ice bath (2 hrs) then at ambient temperature for 15 hrs. To this mixture a 5% aqueous solution of citric acid is added. The organic phase is washed with a 5% aqueous solution of sodium bicarbonate, with a saturated aqueous solution of sodium chloride. The organic phase is dried over Na2SO4 and evaporated to dryness. The oily product is obtained.

Workup

  1. temperaturewith cooling in an ice bath
  2. temperaturewhilst cooling the reaction mixture in an ice bath (2 hrs)
  3. washThe organic phase is washed with a 5% aqueous solution of sodium bicarbonate, with a saturated aqueous solution of sodium chloride
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customevaporated to dryness
  6. customThe oily product is obtained

Sources & evidence

ORD record
ord-4376610327f248dc9c75489f02bee745
Source dataset
uspto-grants-1988_09
Patent number
US04774319

Reaction notes

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