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Diisopropylethylamine → (S)-3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-2-[2-ethyl-3-(3-oxo-morpholin-4-yl)-benzenesulfonylamino]-propionic acid methyl ester

HRID 76801
Notes
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Reaction equation

HRID 76801 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([NH2:17])[CH2:5][C:6]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[O:8][N:7]=1.CCN(C(C)C)C(C)C.[CH2:28]([C:30]1[C:35]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][C:37]2=[O:42])=[CH:34][CH:33]=[CH:32][C:31]=1[S:43](Cl)(=[O:45])=[O:44])[CH3:29]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([NH:17][S:43]([C:31]1[CH:32]=[CH:33][CH:34]=[C:35]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][C:37]2=[O:42])[C:30]=1[CH2:28][CH3:29])(=[O:45])=[O:44])[CH2:5][C:6]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[O:8][N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 66911101(S)-2-Amino-3-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-yl]-propionic acid methyl esterHCID 727928892-Ethyl-3-(3-oxomorpholino)benzene-1-sulfonyl chloride2×

Product 1

HCID 66911103(S)-3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-yl]-2-[2-ethyl-3-(3-oxo-morpholin-4-yl)-benzenesulfonylamino]-propionic acid methyl ester

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

Procedure

Intermediate 2 (860 mg, 3 mmol) was dissolved in 15 ml DCM and DIPEA (2.041 ml, 12 mmol). 2-ethyl-3-(3-oxo-morpholin-4-yl)-benzenesulfonyl chloride, Intermediate 6 (911 mg, 3 mmol) in 10 ml DCM was slowly added and the reaction was stirred at RT overnight. After that 300 μl DIPEA were added and the reaction mixture was heated to 40° C. for 30 min. Then the solution was evaporated to dryness, dissolved in ethyl acetate, washed with 1 N HCl, sat. aq. NaHCO3 and brine. The combined organic layers were dried with MgSO4, filtered and evaporated to dryness. The crude product (1.5 g) was used without further purification in the next step.

Workup

  1. temperaturethe reaction mixture was heated to 40° C. for 30 min
  2. customThen the solution was evaporated to dryness
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with 1 N HCl, sat. aq. NaHCO3 and brine
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product (1.5 g) was used without further purification in the next step

Sources & evidence

ORD record
ord-b2961fd5834e4dc08ce0b2adb3a03e54
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835653B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes