Diisopropylethylamine → HCID 131714300, compound

HRID 484930Notes

Reaction equation

HRID 484930 reaction equation
N#N.C(N[C@@H](C(NCCCC1C=CC=CC=1)=[O:9])C)C.FC1C(OC(=O)[C@H](CC2C=CC(OCC3C=CC=CC=3)=CC=2)NC(OCC2C=CC=CC=2)=O)=C(F)C(F)=C(F)C=1F.C(N(C(C)C)CC)(C)C.[CH2:70]([O:77][C:78]([NH:80][C@H:81]([C:97]([N:99]([CH2:114][CH3:115])[C@@H:100]([C:102]([NH:104][CH2:105][CH2:106][CH2:107][C:108]1[CH:113]=[CH:112][CH:111]=[CH:110][CH:109]=1)=[O:103])[CH3:101])=[O:98])[CH2:82][C:83]1[CH:88]=[CH:87][C:86]([O:89][CH2:90][C:91]2[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=2)=[CH:85][CH:84]=1)=[O:79])[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1>O1CCCC1.CN(C)C=O>[NH:80]([C:78]([O:77][CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)=[O:79])[C@H:81]([C:97]([N:99]([CH2:114][CH3:115])[C@@H:100]([C:102]([NH:104][CH2:105][CH2:106][CH2:107][C:108]1[CH:109]=[CH:110][CH:111]=[CH:112][CH:113]=1)=[O:103])[CH3:101])=[O:98])[CH2:82][C:83]1[CH:88]=[CH:87][C:86]([O:89][C:90]([C:91]2[CH:92]=[CH:93][CH:94]=[CH:95][CH:96]=2)=[O:9])=[CH:85][CH:84]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 13118740HCID 13118740, compound2×HCID 86740231HCID 86740231, compoundHCID 131714301HCID 131714301, compound

Product 1

HCID 131714300HCID 131714300, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N2 -ethyl-N-(3-phenylpropyl)-D-alaninamide (2.71 g.), N-benzyloxycarbonyl-O-benzyl-L-tyrosine pentafluorophenyl ester (5.71 g.) and diisopropylethylamine (1.29 g.) in tetrahydrofuran (65 ml.) was stirred overnight at room temperature. Dimethylformamide (10 ml.) and more N-benzyloxycarbonyl-O-benzyl-L-tyrosine pentafluorophenyl ester (5.71 g.) were added, stirring was continued over the weekend, and the mixture was concentrated. A solution of the residual syrup in ethyl acetate was washed with water, dilute hydrochloric acid, aqueous sodium chloride, aqueous sodium hydroxide (1N, 20 ml.) and aqueous sodium chloride again, then dried and stripped of ethyl acetate. High pressure liquid chromatography of the residue (9.2 g.) on silica gel (350 g.) using hexane-ethyl acetate (55:45) as the eluant (200 ml./min.) afforded in the fractions having a k' value range of 2.5-4.5 (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-N2 -ethyl-N-(3-phenylpropyl)-D-alaninamide as a syrup which crystallized (2.291 g.).

Workup

  1. concentrationthe mixture was concentrated
  2. washA solution of the residual syrup in ethyl acetate was washed with water, dilute hydrochloric acid, aqueous sodium chloride, aqueous sodium hydroxide (1N, 20 ml.) and aqueous sodium chloride again
  3. customdried
  4. customafforded in the fractions
  5. customcrystallized (2.291 g.)

Sources & evidence

ORD record
ord-6532db9a58b940008b8f58732085c68f
Source dataset
uspto-grants-1985_08
Patent number
US04533655

Reaction notes

Loading…