Triethylamine → Z-Val-Pro-Val-Pro-OtBu

HRID 882696Notes

Reaction equation

HRID 882696 reaction equation
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10](O)=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:53][C@H:54]([C:58]([N:60]1[CH2:71][CH2:70][CH2:69][C@H:61]1[C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])=[O:59])[CH:55]([CH3:57])[CH3:56].Cl.C(N(CC)CC)C>ClCCl>[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH:53][C@H:54]([C:58]([N:60]1[CH2:71][CH2:70][CH2:69][C@H:61]1[C:62]([O:64][C:65]([CH3:66])([CH3:68])[CH3:67])=[O:63])=[O:59])[CH:55]([CH3:57])[CH3:56])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10783923Z-Val-pro-OHHCID 90474012H-Val-Pro-OtBu . HCl

Product 1

HCID 131729873Z-Val-Pro-Val-Pro-OtBuYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Z-Val-Pro-OH (681.3 mg, 1.95 mmol) in dichloromethane (6 mL), was successively treated at room temperature. with (benzotriazol-1-yloxy)tris(dimethylamino)phosphoniun hexafluorophale (BOP) (865.1 mg, 1.95 mmol), H-Val-Pro-OtBu.HCl (500 mg, 1.63 mmol) and triethylamine (TEA) (500 μL, 3.58 mmol). The mixture was stirred overnight at room temperature. Then, the solvent was evaporated, the residue was dissolved in dichloromethane and washed with citric acid (10%), NaHCO3 (10%) and brine. The organic layer was dried (Na2SO4) and evaporated to dryness leaving a residue that was purified on a column chromatography with hexane-ethyl acetate, 2:1 to give X (68% yield).

Workup

  1. customThen, the solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with citric acid (10%), NaHCO3 (10%) and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated to dryness
  6. customleaving a residue that
  7. customwas purified on a column chromatography with hexane-ethyl acetate, 2:1
  8. customto give X (68% yield)

Sources & evidence

ORD record
ord-0d7b8949bac64990ba4c4265cf0128e1
Source dataset
uspto-grants-2012_08
Patent number
US08236756B2

Reaction notes

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