Methyl N-(oxomethylidene)-L-leucinate → HCID 69001166, compound

HRID 229835Notes

Reaction equation

HRID 229835 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([C:13](=[O:24])[NH:14][C@H:15]1[CH2:21][CH2:20][C@@H:19]([CH3:22])[NH:18][CH2:17][CH:16]1[OH:23])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[CH3:26][O:27][C:28](=[O:37])[C@@H:29]([N:34]=[C:35]=[O:36])[CH2:30][CH:31]([CH3:33])[CH3:32]>C1COCC1>[CH3:26][O:27][C:28](=[O:37])[C@@H:29]([NH:34][C:35]([N:18]1[CH2:17][CH:16]([OH:23])[C@@H:15]([NH:14][C:13](=[O:24])[C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:25])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:21][CH2:20][C@H:19]1[CH3:22])=[O:36])[CH2:30][CH:31]([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 7019163Methyl N-(oxomethylidene)-L-leucinateHCID 69003467HCID 69003467, compound

Product 1

HCID 69001166HCID 69001166, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[(S)-3-Methyl-1-((4S,7R)-7-methyl-3-hydroxy-azepan-4-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester (Example 12a-i, 500 mg, 1.4 mmol) was dissolved in THF (7 ml), then (S)-(−)-2-isocyanato-4-methylvaleric acid methyl ester (180 mg, 1.05 mmol) was added and the reaction mixture was stirred at RT for 2 h. The reaction mixture was concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 1% to 2% MeOH/CH2Cl2) to yield the title compound as a white solid (91%, 506 mg): LC/Electrospray mass spec: M+H+=529.4.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo by rotary evaporation
  2. customchromatographed (silica gel, 1% to 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1433e1dffcf34e2295061107a2cb4f13
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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