Hydrochloric Acid → HCID 88962800, compound

HRID 1775746Notes

Reaction equation

HRID 1775746 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH2:8][S:9][CH3:10])[NH2:6].C(N(CC)CC)C.[C:19]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20]1.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([NH:6][C:19](=[O:25])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:8][S:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 88962800HCID 88962800, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Compound 2 (0.25 g, 1 eq.) was suspended in CH2Cl2 (12.5 ml, C=0.1M). Triethylamine (0.26 ml, 1.5 eq.) was added to the solution which was then stirred for 10 minutes. After stirring 4-dimethylamino pyridine (0.015 g, 0.1 eq.) and succinic anhydride (0.125 g, 1 eq.) were added and the reaction left to stir for 16 hours at room temperature. The reaction mixture was then shaken with 3×20 ml portions of hydrochloric acid (2M), the aqueous washings were subsequently extracted with 3×20 ml portions of diethyl ether. The DCM portion was discarded and the ether layers were combined and dried over anhydrous MgSO4, filtered and evaporated to yield a white solid 3 (0.199 g, 60% yield).

Workup

  1. additionwere added
  2. waitthe reaction left
  3. stirringto stir for 16 hours at room temperature
  4. extractionthe aqueous washings were subsequently extracted with 3×20 ml portions of diethyl ether
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8011a69bb2334d898919ad4603a991dc
Source dataset
uspto-grants-2016_02
Patent number
US09260460B2

Reaction notes

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