Benzylamine → HCID 67278285, compound

HRID 1695701Notes

Reaction equation

HRID 1695701 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5](Br)[CH2:6][N:7]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH2:8][CH:9](Br)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:2].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:5]1[CH2:6][N:7]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:8][CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:34]1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26])[CH3:2]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 72471572HCID 72471572, compound

Product 1

HCID 67278285HCID 67278285, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (SR)-3-[benzenesulfonyl-((SR)-2-bromo-2-ethoxycarbonyl-ethyl)-amino]-2-bromo-propionic acid ethyl ester (CAS 58661-68-0) (13.8 g, 26.8 mmol) in toluene (54 ml) was added benzylamine (8.81 ml, 80.4 mmol) and the mixture was stirred at 90° C. for 1.5 h. Cooled to 23° C., filtered the solid off, washed with toluene and the filtrate was evaporated to leave a crude product which was purified by silica gel column chromatography with tert-butyl methyl ether and n-heptane 3:7 to give the title compound as light yellow crystals (7.0 g, 57%), MS (ISP) m/e=461.2 [(M+H)+].

Workup

  1. temperatureCooled to 23° C.
  2. filtrationfiltered the solid off,
  3. washwashed with toluene
  4. customthe filtrate was evaporated
  5. customto leave a crude product which
  6. customwas purified by silica gel column chromatography with tert-butyl methyl ether and n-heptane 3:7

Sources & evidence

ORD record
ord-618e95570e9b42c891a1d3f7ff864a1c
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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