L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → HCID 71105111, compound

HRID 242387

Reaction equation

HRID 242387 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([C:16](=[O:18])[CH3:17])[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=1.[NH:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:20]([C:25]([OH:27])=O)[CH2:21][CH:22]([CH3:24])[CH3:23].CCN=C=N[CH2:40][CH2:41][CH2:42]N(C)C.Cl>ClCCl.CN(C1C=CN=CC=1)C>[C:16]([C:5]1[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:14])([CH3:13])[CH3:15])[CH:7]=[C:3]([CH2:2][O:1][C:25](=[O:27])[C@@H:20]([NH:19][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:21][C:22]2[CH:23]=[CH:42][CH:41]=[CH:40][CH:24]=2)[N:4]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 710869721-(4-hydroxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl)ethanone

Product 1

HCID 71105111HCID 71105111, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The compound (2.00 g) obtained in (3) was dissolved in dichloromethane (10 mL), and Boc-Leu-OH (2.21 g), EDC.HCl (2.13 g), and DMAP (0.99 g) were added while stirring. After the stirring was continued for 1 day, the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/chloroform=0%→25%) using silica gel column (product name: Hi-Flash Column 3 L, manufactured by Yamazen Corporation) to afford the title compound (3.20 g).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resulting residue was purified by flash chromatography (ethyl acetate/chloroform=0%→25%)

Sources & evidence

ORD record
ord-ee60c6e8bc1744969018dda8e777ca7c
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Linked notes

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