Iodoethane → Boc-D-alanine Ethyl Ester

HRID 1449767Notes

Reaction equation

HRID 1449767 reaction equation
[CH2:1](I)[CH3:2].[CH3:4][C@@H:5]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:6]([OH:8])=[O:7]>>[C:13]([O:12][C:10]([NH:9][C@@H:5]([C:6]([O:8][CH2:1][CH3:2])=[O:7])[CH3:4])=[O:11])([CH3:14])([CH3:15])[CH3:16]

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 637606BOC-D-alanine

Product 1

HCID 12515028Boc-D-alanine Ethyl EsterYield 48.8%

Procedure

The title compound was prepared by the method of Example 8 using ethyl iodide (2.4 mL, 30 mmol) instead of methyl iodide and BOC--D--Ala--OH (5.0 g, 26.4 mmol) instead of the product of Example 1. Concentration afforded the title compound (2.8 g) as a pale yellow oil and the structure verified by NMR.

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-0dc0189d410e496f8db98ffd16476986
Source dataset
uspto-grants-1997_02
Patent number
US05599947

Reaction notes

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