Dichloromethane → Diisopropylethylamine

HRID 1919392Notes

Reaction equation

HRID 1919392 reaction equation
[C:1](OC(=O)C)(=O)C.C(Cl)(=O)C.ClCCl.O1[CH2:19][CH2:18][CH2:17]C1.C([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])C>N1C=CC=CC=1>[CH:18]([N:22]([CH:23]([CH3:24])[CH3:1])[CH2:25][CH3:26])([CH3:19])[CH3:17]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471Triethylamine

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Free amine 57 can be converted to the corresponding protected intermediate 58 by reaction with an acetylation agent such as acetic anhydride (Ac2O) or acetyl chloride (AcCl) in a solvent such as dichloromethane (DCM), tetrahydrofuran (THF), or pyridine, optionally in the presence of a base such as pyridine, triethylamine (Et3N, TEA), or diisopropylethylamine (iPr2EtN, DIEA) and/or a nucleophilic acylation catalyst such 4-(N,N-dimethylaminopyridine (DMAP) at temperature from about −20° C. to about 40° C. to provide corresponding protected sulfonyl ester intermediate 58.

Sources & evidence

ORD record
ord-abbbf09aa210479596c1dd6580577633
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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