Hydrochloric Acid → Z-N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2Me

HRID 1988240Notes

Reaction equation

HRID 1988240 reaction equation
[NH:1]([CH3:22])[C@H:2]([C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[C:23]([N:33]([CH3:41])[C@H:34]([C:38]([OH:40])=O)[CH:35]([CH3:37])[CH3:36])([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24].O.Cl>C1COCC1>[C:23]([N:33]([CH3:41])[C@H:34]([C:38]([N:1]([CH3:22])[C@H:2]([C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:5]=1)=[O:40])[CH:35]([CH3:36])[CH3:37])([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 131727507N-Me-Tyr(3-t-Bu)-NHSO2Me

Product 1

HCID 131727506Z-N-Me-Val-N-Me-Tyr(3-t-Bu)-NHSO2MeYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude N-Me-Tyr(3-t-Bu)-NHSO2Me (0.51 g, 1.43 mmol), Z-N-Me-Val-OH 0.49 g, 1.86 mmol) and CMPI (0.51 g, 2.00 mmol) in THF (10 ml), TEA (0.60 ml, 4.29 mmol) was added under cooling with ice and stirred at room temperature overnight. The reaction mixture was mixed with water, rendered acidic by the addition of 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=2:3 containing 0.5% acetic acid) to give the titled compound (0.70 g, in 2 steps, 85%).

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 magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-27a2dd35c4b941e0af89ee128a266e4f
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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