Triethylamine → HCID 123486882, compound

HRID 625701Notes

Reaction equation

HRID 625701 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1)([OH:3])=O.C(Cl)(=O)C(Cl)=O.[OH:19][C:20]([CH3:24])([CH3:23])[CH2:21][NH2:22].C(N(CC)CC)C>ClCCl.CN(C)C=O.Cl>[OH:19][C:20]([CH3:24])([CH3:23])[CH2:21][NH:22][C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1)=[O:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 951022-Propanol, 1-amino-2-methyl-HCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 123486882HCID 123486882, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-Carboxyphenylboronic acid (0.5 g, 3.0 mmol) is suspended in dry dichloromethane (8 mL) and oxalylchloride (2 M in dichloromethane, 3.0 mL, 6.0 mmol) is added followed by 2 drops of N,N-dimethylformamide. The mixture is stirred for 3 hours then the solvent removed under vacuum. 2-Hydroxy-2-methylpropylamine (step 1, 800 mg, 9.0 mmol) and triethylamine (2.0 mL, 13.8 mmol) in dichloromethane (12 mL) are added to the residue and the mixture stirred for 30 minutes. The mixture is diluted with 1 M HCl and the phases separated. The aqueous layer is extracted several times with ethyl acetate. The combined organic phases are dried and the solvent removed to give the title compound as a crude product. LC (METHOD 5): tR=0.55 min; Mass spectrum (ES+): m/z=238 [M+H]+.

Workup

  1. customthe solvent removed under vacuum
  2. stirringthe mixture stirred for 30 minutes
  3. customthe phases separated
  4. extractionThe aqueous layer is extracted several times with ethyl acetate
  5. customThe combined organic phases are dried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-bea1130ceafc4e859f6ba165ea93b2ca
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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