Diisopropylethylamine → HCID 54120602, compound

HRID 1953906Notes

Reaction equation

HRID 1953906 reaction equation
[C:1]([O:5][C:6](=[O:14])[C@@H:7]([NH:12][CH3:13])[CH2:8][CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:24]([C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>C1COCC1>[C:1]([O:5][C:6](=[O:14])[C@@H:7]([N:12]([CH2:32][C:31]1[CH:34]=[CH:35][C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:29][CH:30]=1)[CH3:13])[CH2:8][CH:9]([CH3:10])[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 11020929HCID 11020929, compound

Product 1

HCID 54120602HCID 54120602, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

(S)-4-Methyl-2-methylamino-pentanoic acid tert-butyl ester (6 g, 29.8 mmol) was dissolved in THF (250 mL) and treated with diisopropylethylamine (7.8 mL, 44.7 mmol) and p-t-butyl-benzyl bromide (6.03 mL, 32.8 mL). The reaction was heated to 40° C. overnight, then filtered and concentrated. The residue was chromatographed on silica gel eluting with 5% EtOAc/hexanes to give 5.1 g (50%) of (S)-2-[(4-tert-Butyl-benzyl)-methyl-amino]-4-methyl-pentanoic acid tert-butyl ester.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was chromatographed on silica gel eluting with 5% EtOAc/hexanes

Sources & evidence

ORD record
ord-7f13b40372ce4bfebfbc6a5a7a90a88d
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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