Water → Boc-Phe(4-Cl)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1988234Notes

Reaction equation

HRID 1988234 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[NH:21]([CH3:46])[C@H:22]([C:26]([N:28]([CH3:45])[C@H:29]([C:42]([NH2:44])=[O:43])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:32]=1)=[O:27])[CH:23]([CH3:25])[CH3:24].O>C1COCC1>[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11]([N:21]([CH3:46])[C@H:22]([C:26]([N:28]([CH3:45])[C@H:29]([C:42]([NH2:44])=[O:43])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C:38]([CH3:41])([CH3:39])[CH3:40])[CH:32]=1)=[O:27])[CH:23]([CH3:25])[CH3:24])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2734499N-(tert-Butoxycarbonyl)-4-chloro-L-phenylalanineHCID 131722752N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Product 1

HCID 131727503Boc-Phe(4-Cl)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Boc-Phe(4-Cl)-OH (354 mg, 1.18 mmol), N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.33 g, 0.908 mmol) and CMPI (301 mg, 1.18 mmol) in THF (8 ml), TEA (0.38 ml, 2.72 mmol) was added under cooling with ice and stirred at room temperature overnight. The reaction mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: chloroform:methanol:aqueous ammonia=40:1:0.05) to give Boc-Phe(4-Cl)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.45 g, 77%).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-a54ac501124f43a9811ee1750d928657
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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