Benzyl Bromide → HCID 54182839, compound

HRID 1532034Notes

Reaction equation

HRID 1532034 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[C:15]([O:22][CH2:23][CH3:24])=[N:16][O:17][C:18]=1[C:19]([OH:21])=[O:20])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.N12CCCN=[C:39]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2.[CH:44]1C=CC=CC=1.O1CCCC1>>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[C:15]([O:22][CH2:23][CH3:24])=[N:16][O:17][C:18]=1[C:19]([O:21][CH2:44][C:39]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:20])[C:10]([O:12][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21251164HCID 21251164, compoundHCID 22633675Benzene tetrahydrofuran

Product 1

HCID 54182839HCID 54182839, compoundYield 86%

Procedure

A mixture of (RS)-2-[(tert-butoxycarbonyl)amino]-3-(5-carboxy-3-ethoxyisoxazol-4yl)propionic acid (1.4 g, 4.1 mmol), benzyl bromide (1.4 g, 8.2 mmol) in benzene/tetrahydrofuran (4:1) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.3 g, 8.6 mmol) and the resulting mixture was boiled under reflux for 3 h. The mixture was filtered and evaporated in vacuo. Flash chromatography (SiO2, eluent:, ethyl acetate/heptane (1:3)) gave benzyl (RS)-2-[(tert-butoxycarbonyl)amino]-3-(5-benzyloxycarbonyl-3-ethoxyisoxazol-4-yl)propionate as an oil (1.9 g, 86%).

Workup

  1. temperatureunder reflux for 3 h
  2. filtrationThe mixture was filtered
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-7c8f9d3021b1494abb18943a31e4b029
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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