Methanesulfonyl chloride → HCID 46181731, compound

HRID 1776610Notes

Reaction equation

HRID 1776610 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][S:23]([CH3:22])(=[O:25])=[O:24])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 7019130Boc-Tyr-OMe

Product 1

HCID 46181731HCID 46181731, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate (500 mg, 1.7 mmol) was dissolved in DCM (10 ml), and TEA (343 mg, 3.4 mmol) and methanesulfonyl chloride (290 mg, 2.6 mmol) were added. The mixture was stirred at RT for 2 hours, then was washed with HCl 1N (2×). The organic layer was dried over Na2SO4 and evaporated under vacuum to give 570 mg (90%) of the title compound which was employed in the next step without any further purification. MS/ESI+ 374.12 [MH]+.

Workup

  1. washwas washed with HCl 1N (2×)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-96738f82a6354ddb9635afb32ad04a14
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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