Isopropyl chloroformate → HCID 70118438, compound

HRID 1977583Notes

Reaction equation

HRID 1977583 reaction equation
[CH:1]1([CH2:5][C@H:6]([C:8]([OH:10])=[O:9])[NH2:7])[CH2:4][CH2:3][CH2:2]1.Cl[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13]>[OH-].[Na+].O1CCOCC1>[CH:15]([O:14][C:12]([NH:7][C@@H:6]([C:8]([OH:10])=[O:9])[CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)=[O:13])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 7917Isopropyl chloroformateHCID 509993233-Cyclobutyl-D-alanine

Product 1

HCID 70118438HCID 70118438, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

0.57 g (4 mmol) of 3-cyclobutyl-D-alanine is dissolved in 8 ml 1:1 mixture of 1M NaOH solution and dioxane. The mixture is cooled to 0° C. and simultaneously 4 ml of 1M NaOH solution and 4 ml of isopropyl chloroformate (conc. 1M in toluene) solution are added with vigorous stirring. The reaction mixture is stirred for 1 hour at this temperature and for 5 hours at room temperature.

Sources & evidence

ORD record
ord-d4f6a5b74f784ad09b5d690a27e34d99
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

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