Citric Acid → HCID 67262986, compound

HRID 1898743Notes

Reaction equation

HRID 1898743 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:21])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([C:18](Cl)=[O:19])([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:31]([NH2:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.CCOC(C)=O>[C:1]([O:4][C:5]1[C:6]([CH3:21])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([C:18](=[O:19])[NH:37][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8102HexylamineHCID 81531DiisopropylethylamineHCID 11001420HCID 11001420, compound

Product 1

HCID 67262986HCID 67262986, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To one of the above aliquots of crude 2-(chlorocarbonyl)-2,5,7,8-tetramethylchroman-6-yl acetate in 10 mL CH2Cl2 was added 1.0 mL diisopropylethylamine followed by 315 mg 1-hexylamine and overnight stiffing. The reaction mixture was poured into 1.0 M citric acid and 50 mL EtOAc added. The organic layer was separated and purified by flash chromatography to give 781 mg of 2-(hexylcarbamoyl)-2,5,7,8-tetramethylchroman-6-yl acetate, as a clear syrup. MS (m/z): M+376.3

Workup

  1. additionadded
  2. customThe organic layer was separated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7adab3c017b04a5ba50a23cc1603832a
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

Loading…