1-Hydroxybenzotriazole → HCID 59620370, compound

HRID 1887771Notes

Reaction equation

HRID 1887771 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][O:17][C:18](=[O:25])[C@@H:19]([CH2:21][CH:22]([CH3:24])[CH3:23])[NH2:20].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[CH3:16][O:17][C:18](=[O:25])[C@H:19]([NH:20][C:10](=[O:12])[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])([CH3:14])[CH3:13])[CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 11600782D-Leucine Methyl Ester Hydrochloride

Product 1

HCID 59620370HCID 59620370, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-(tert-Butoxycarbonylamino)-2-methylpropanoic acid (22.4 g) and D-leucine methyl ester hydrochloride (20.0 g) were dissolved in N,N-dimethylformamide (224 mL), and triethylamine (11.1 g) was added dropwise thereto under cooling on ice. To the mixture were sequentially added 1-hydroxybenzotriazole (14.9 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (19.1 g), and stirring was performed for two hours. Water (224 mL) was added to the reaction mixture, and the formed precipitates were recovered through filtration, whereby the title compound (57.8 g) was yielded as wet crystals.

Workup

  1. temperatureunder cooling on ice
  2. customthe formed precipitates
  3. filtrationwere recovered through filtration, whereby the title compound (57.8 g)
  4. customwas yielded as wet crystals

Sources & evidence

ORD record
ord-f83237c7c74b45268611a45b3f95de21
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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