HCID 22816344, compound → HCID 22816343, compound

HRID 1680579Notes

Reaction equation

HRID 1680579 reaction equation
C[O:2][C:3](=[O:28])[C@H:4]([C@@H:25]([CH3:27])[OH:26])[NH:5][C:6](=[O:24])[C@H:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>[OH-].[K+]>[C:9]([NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:28])=[O:2])[C@@H:25]([CH3:27])[OH:26])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

3

Reactant 1

HCID 22816344HCID 22816344, compound

Product 1

HCID 22816343HCID 22816343, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

19.6 Grams of Boc-L-tyrosyl-L-threonine methyl ester are dissolved in 75 ml of 2 M potassium hydroxide solution at room temperature. After 30 minutes the aqueous solution is extracted with 20 ml of ethyl acetate, acidified with cold 1 M potassium bisulfate, and extracted with four 25 ml portions of ethyl acetate. The combined extracts are washed with saturated sodium chloride solution, dried over sodium sulfate and filtered. The solvent is removed under reduced pressure to give Boc-L-tyrosyl-L-threonine.

Workup

  1. extractionAfter 30 minutes the aqueous solution is extracted with 20 ml of ethyl acetate
  2. extractionextracted with four 25 ml portions of ethyl acetate
  3. washThe combined extracts are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f7b5e3fda0a2414da52694bceb275a22
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Reaction notes

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