Triethylamine → HCID 58066687, compound

HRID 390413Notes

Reaction equation

HRID 390413 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[CH2:11][S:12][C:13]([CH3:16])([CH3:15])[CH3:14].[CH2:18](N(CC)CC)C.[C:25](Cl)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].CCOC(C)=O>C(Cl)Cl.O>[CH2:1]([O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:6][C:5]=1[CH2:11][S:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH3:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62493Pivaloyl chlorideHCID 66682864HCID 66682864, compound

Product 1

HCID 58066687HCID 58066687, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-2-tert-butylsulfanylmethyl-benzoic acid methyl ester (5.1 g, 19.1 mmol) and triethylamine (6.6 mL, 47.8 moml) were combined in CH2Cl2 (200 mL) and cooled to 0° C. Pivaloyl chloride (2.8 mL, 22.9 mmol) was added dropwise by syringe, and the reaction was stirred at room temperature for 1 hour. The mixture was worked up with EtOAc and H2O to give the title compound.

Sources & evidence

ORD record
ord-30c550d73cd8401bad01890ab2579d90
Source dataset
uspto-grants-2013_02
Patent number
US08383654B2

Reaction notes

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