Triethylamine → N-dodecyl-2-carbobenzyloxyaminosuccinamic acid

HRID 2040598Notes

Reaction equation

HRID 2040598 reaction equation
[C:1]([NH:11][C@@H:12]1[C:17](=[O:18])[O:16][C:14](=[O:15])[CH2:13]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:19]([NH2:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(N(CC)CC)C>C(Cl)Cl>[CH2:19]([NH:31][C:14](=[O:15])[CH2:13][CH:12]([NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])[C:17]([OH:16])=[O:18])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13583DodecylamineHCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

Product 1

HCID 57925483N-dodecyl-2-carbobenzyloxyaminosuccinamic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Carbobenzyloxy-L-aspartic anhydride (1 mmol) was dissolved in 50 mL methylene chloride, followed by the addition of 1.05 eq of dodecylamine and 1.1 eq of triethylamine. The reaction was capped to prevent evaporation, and stirred for 12 hours. When no trace of starting material could be detected by thin layer chromatography (TLC) (CH2Cl2, 5% MeOH), the reaction was quenched with 20 mL 1N hydrochloric acid followed by extraction with chloroform (5×). The organic layer was dried over magnesium sulfate, and 7 was obtained as a white solid (yield 97%).

Workup

  1. customThe reaction was capped
  2. customevaporation
  3. customthe reaction was quenched with 20 mL 1N hydrochloric acid
  4. extractionfollowed by extraction with chloroform (5×)
  5. dry with materialThe organic layer was dried over magnesium sulfate

Sources & evidence

ORD record
ord-ca57fe46a0dc4bf5a4f92c9287deb37b
Source dataset
uspto-grants-2013_11
Patent number
US08580923B2

Reaction notes

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