Diisopropylethylamine → HCID 131719353, compound

HRID 1441185Notes

Reaction equation

HRID 1441185 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.[NH:28]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:29]([C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[CH2:30][C:31](=[O:33])O.[NH:51](CC)[CH2:52][CH3:53].Cl.CCN(C(C)C)C(C)C.CCCCCC.C[CH2:73][O:74][C:75](C)=[O:76]>C(Cl)Cl>[NH:28]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:29]([C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[CH2:30][C:31]([N:51]([C:75]([O:74][CH2:73][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:76])[CH2:52][CH3:53])=[O:33]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7017887(3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acidHCID 10197650Diethylammonium chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 131719353HCID 131719353, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BOP (2.20g, 5.0 mmol) was added under N2 to a cooled (0°) solution of Boc-Asp-OBzl (1.90 g, 4.6 mmol) in CH2Cl2 (50 ml). After 3 min NHEt2.HCl (0.55 g, 5.0 mmol) and DIPEA (2.4 ml, 1.38 mmol) were added. The resultant solution was stirred at 20°-22° for 18 h. The solution was washed with 10% aqueous citric acid (2 ×), 10% aqueous NaHCO3 (2 ×) and brine (2 ×). The organic layer was dried (MgSO4) and concentrated to give an oil. After SiO2 chromatography of the oil using hexane-EtOAc (7:3) as the eluent, Boc-Asp(NEtz)-OBzl (1.55 g, 89%) was obtained as an oil. Under a N2 atmosphere, a solution of the latter compound (1.55 g, 4.09 mmol) in MeOH (100 ml) was mixed with 5% Pd/C (155 mg). The mixture was shaken on a Parr apparatus under H2 (50 psi) for 90 min. The mixture was filtered through a 45 m membrane and the filtrate concentrated to give Boc7Asp(NEta)-OH (1.15 g, 98%) as an oil. The structure of the product was confirmed by NMR.

Workup

  1. washThe solution was washed with 10% aqueous citric acid (2 ×), 10% aqueous NaHCO3 (2 ×) and brine (2 ×)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customto give an oil

Sources & evidence

ORD record
ord-accf08f7eb914f169ee687c501b2d761
Source dataset
uspto-grants-1996_03
Patent number
US05502036

Reaction notes

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