Pyridine → HCID 86638961, compound

HRID 1512021Notes

Reaction equation

HRID 1512021 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1.O[CH2:35][CH2:36][CH2:37][C@@H:38]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[NH:39][C:40]([O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])=[O:41]>C(Cl)Cl>[Br:1][CH2:35][CH2:36][CH2:37][C@@H:38]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[NH:39][C:40]([O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])=[O:41]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 86638959HCID 86638959, compound

Product 1

HCID 86638961HCID 86638961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of N-bromosuccinimide (2.129 g, 11.96 mmol) in DCM (10 ml) was treated with triphenylphosphine (2.93 g, 11.17 mmol) in DCM (10 ml), followed by pyridine (0.387 ml, 4.79 mmol) and tert-butyl 5-hydroxy-N-{[2-(trimethylsilyl)ethoxy]carbonyl}-L-norvalinate (1.33 g, 3.99 mmol) in DCM (5 ml). The resulting black mixture was stirred at room temp for 24 h. The mixture was pre-absorbed onto SiO2 and purified by chromatography (silica gel, 0-5-10-20% Et2O/isohexane) to afford tert-Butyl 5-bromo-N-{[2-(trimethylsilyl)ethoxy]carbonyl}-L-norvalinate Intermediate 5 (1.1 g) as a colourless oil.

Workup

  1. customThe mixture was pre-absorbed onto SiO2
  2. custompurified by chromatography (silica gel, 0-5-10-20% Et2O/isohexane)

Sources & evidence

ORD record
ord-13e66bb0aab74833805c6f831b6ddb05
Source dataset
uspto-grants-2012_07
Patent number
US08217050B2

Reaction notes

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