HCID 131727519, compound → HCID 57729145, compound

HRID 1988287Notes

Reaction equation

HRID 1988287 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:12]([N:14]([CH3:39])[C@H:15]([C:19]([N:21]([CH3:38])[C@H:22]([C:35]([NH2:37])=[O:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=1)=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]([C:12]([N:14]([CH3:39])[C@H:15]([C:19]([N:21]([CH3:38])[C@H:22]([C:35]([NH2:37])=[O:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C:31]([CH3:32])([CH3:34])[CH3:33])[CH:25]=1)=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1

Participants

4

Reactant 1

HCID 131727519HCID 131727519, compound

Product 1

HCID 57729145HCID 57729145, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of Boc-Tyr(3-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.19 g, 0.294 mmol) in methylene chloride (3 ml), TFA (1.5 ml) was added and stirred for 15 min. The reaction mixture was concentrated under reduced pressure, mixed with a saturated aqueous NaHCO3 solution, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The resultant was evaporated to remove the solvent under reduced pressure, giving the titled compound (136 mg, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionmixed with a saturated aqueous NaHCO3 solution
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe resultant was evaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-cb9ceeada75c42e8be30120d0a57e7ed
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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