Diisopropylethylamine → HCID 131733471, compound

HRID 2278810Notes

Reaction equation

HRID 2278810 reaction equation
[NH2:1][C@@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[NH2:16][C@H:17]([C:28]([O:30][CH3:31])=[O:29])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.Cl.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C@@H:2]([C:13]([NH:16][C@H:17]([C:28]([O:30][CH3:31])=[O:29])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)=[O:14])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 679497p-Nitro-D-phenylalanineHCID 2724699PyBOPHCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Product 1

HCID 131733471HCID 131733471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g (5.39 mmol) Chas-D-Phe(4-NO2)—OH and 1.42 g (5.39 mmol) H-Phe(4-NO2)—OMe.HCl were suspended in 30 ml of DMF and 2.82 g (5.39 mmol) of PyBOP and 2.81 ml (16.16 mmol) of DIPEA was added at 0° C. After 2 h of stirring at 0° C., the solvent was removed in vacuo and the brown residue resuspended in 5% KHSO4 soln./EtOAc. The organic phase was washed 3× with 5%-KHSO4 soln., 1× with sat. NaCl soln., 3× with sat. NaHCO3-soln., and 3× with sat. NaCl soln., subsequently dried with MgSO4, filtered, and the solvent was removed in vacuo.

Workup

  1. customthe solvent was removed in vacuo
  2. washThe organic phase was washed 3× with 5%-KHSO4 soln
  3. dry with material, subsequently dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cdea035f35e24810b413ee4f7f8241a2
Source dataset
uspto-grants-2015_09
Patent number
US09133194B2

Reaction notes

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