Triethylamine → HCID 178426666, compound

HRID 2278797Notes

Reaction equation

HRID 2278797 reaction equation
[Cl:1][C:2]1[CH:18]=C(C#N)[CH:16]=[C:15]([CH3:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C([N:24]([CH2:27][CH3:28])CC)C.Cl.[NH2:30][OH:31]>C(O)C>[Cl:1][C:2]1[CH:18]=[C:28]([C:27](=[NH:24])[NH:30][OH:31])[CH:16]=[C:15]([CH3:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 70556803Tert-butyl 4-(2-chloro-4-cyano-6-methylphenoxy)butanoate

Product 1

HCID 178426666HCID 178426666, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 4-(2-chloro-4-cyano-6-methylphenoxy)butanoate (640 mg, 2.07 mmol), triethylamine (418 mg, 4.13 mmol) and hydroxylamine hydrochloride (215 mg, 3.10 mmol) in ethanol (5 mL) is stirred at 65° C. for 72 h. The mixture is concentrated and the crude product is purified by prep. HPLC to give tert-butyl 4-(2-chloro-4-(N-hydroxycarbamimidoyl)-6-methylphenoxy)butanoate (145 mg) as a pale grey solid; LC-MS: tR=0.65 min, [M+H]+=343.20.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe crude product is purified by prep

Sources & evidence

ORD record
ord-4bb52c42e7334806803b3cb3bd3be8d6
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

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