Triethylamine → HCID 46181731, compound

HRID 916902Notes

Reaction equation

HRID 916902 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7019130Boc-Tyr-OMe

Product 1

HCID 46181731HCID 46181731, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

N-Boc-L-tyrosine methyl ester 3 (29.5 g, 0.1 mol) and triethylamine (20.2 g, 0.2 mol) were dissolved in toluene (147.7 g) and then cooled to 0° C. To the mixture was added dropwise methanesulfonyl chloride (13.8 g, 0.12 mol) at 0° C. over 40 min. The mixture was further kept at 0° C. for 25 min. The reaction mass was washed with 5% hydrochloric acid (72.9 g) and 5% aqueous sodium bicarbonate (84.0 g), dried over magnesium sulfate, and then concentrated under reduced pressure with a rotary evaporator. After crystallization from the concentrate mass with n-hexane, precipitated crystals were collected by filtration and dried to give N-Boc-O-methanesulfonyl-L-tyrosine methyl ester 6 (36.0 g, yield 96%) as white crystals.

Workup

  1. washThe reaction mass was washed with 5% hydrochloric acid (72.9 g) and 5% aqueous sodium bicarbonate (84.0 g)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure with a rotary evaporator
  4. customAfter crystallization from the concentrate mass with n-hexane
  5. customprecipitated crystals
  6. filtrationwere collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-a04f894040564d17aa8c9723aabaaa3a
Source dataset
uspto-grants-2007_09
Patent number
US07271280B2

Reaction notes

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