Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl- → HCID 86673200, compound

HRID 1746361Notes

Reaction equation

HRID 1746361 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:40])[CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH3:39].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:18]([NH:17][CH2:16][CH2:15][NH:14][C:10](=[O:12])[CH2:9][N:8]([CH3:13])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:40])[CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH3:39]

Participants

5

Reactant 3

HCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58416605HCID 58416605, compound

Product 1

HCID 86673200HCID 86673200, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-((tert-Butoxycarbonyl)(methyl)amino)acetic acid (240 mg, 1.27 mmol) was taken up in 5 mL of CH2Cl2 along with (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-aminoethyl)docosa-4,7,10,13,16,19-hexaenamide (470 mg, 1.27 mmol), HATU (724 mg, 1.27 mmol). The resulting reaction mixture was stirred at room temperature for 20 h. The organic layer was washed with saturated NH4Cl, brine, dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford 650 mg of tert-butyl (2-((2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)ethyl)amino)-2-oxoethyl)(methyl)carbamate (56% yield).

Workup

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with saturated NH4Cl, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-22303ecba84b441eab03082650e6a53d
Source dataset
uspto-grants-2015_10
Patent number
US09150504B2

Reaction notes

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