Triethylamine → Boc-L-Ile-DL-Pip-OBzl

HRID 2417160Notes

Reaction equation

HRID 2417160 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].[NH:17]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:18]1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].Cl.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([N:17]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:18]1[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66751062Benzyl piperidine-2-carboxylate hydrochloride

Product 1

HCID 131724669Boc-L-Ile-DL-Pip-OBzlYield 115%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-L-Ile-OH ½ H2O (3.92 g, 16.8 mmol), H-D,L-Pip-OBzl HCl (3.57 g, 12 mmol) and HATU (7.75 g, 18 mmol) were dissolved in DMF (15 ml), mixed with Et3N (4.76 ml, 30 mmol) under ice cooling, and then stirred overnight. The reaction mixture was concentrated, extracted with ethyl acetate (120 ml), and washed twice with 10% citric acid, 4% NaHCO3 and then brine, respectively. After drying over magnesium sulfate, ethyl acetate was distilled off. The residue was vacuum dried and purified by flash chromatography (3.5×20 cm) with CHCl3/MeOH (99:1) to yield Boc-L-Ile-D,L-Pip-OBzl (5.90 g, 13.8 mmol; yield 97%) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate (120 ml)
  3. washwashed twice with 10% citric acid, 4% NaHCO3
  4. dry with materialAfter drying over magnesium sulfate, ethyl acetate
  5. distillationwas distilled off
  6. customdried
  7. custompurified by flash chromatography (3.5×20 cm) with CHCl3/MeOH (99:1)

Sources & evidence

ORD record
ord-befb98a70aa1425eb3db42fadc161014
Source dataset
uspto-grants-2004_11
Patent number
US06825317B2

Reaction notes

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