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Triethylamine → 2-(4-but-2-ynyloxy-benzenesulfonylamino)-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl ester

HRID 2104214
Notes
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Reaction equation

HRID 2104214 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:25])[CH:12]([NH2:24])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=2)[NH:16][CH:15]=1)[CH3:9].[CH2:26]([O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1)[C:27]#[C:28][CH3:29]>O.O1CCOCC1>[CH2:8]([O:10][C:11](=[O:25])[CH:12]([NH:24][S:37]([C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:26][C:27]#[C:28][CH3:29])=[CH:36][CH:35]=1)(=[O:39])=[O:38])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=2)[NH:16][CH:15]=1)[CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 14828752Ethyl 2-amino-3-(5-bromo-1H-indol-3-YL)propanoate

Product 1

HCID 578059912-(4-but-2-ynyloxy-benzenesulfonylamino)-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl esterYield 61.4%

Reagents, catalysts & solvents 1

HCID 21886435
1,4-Dioxane--water (1/1)
Solvent

Procedure

Triethylamine (4.81 mL, 34.5 mmol) was added to a mixture of 2-amino-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl ester (4.00 g, 11.51 mmol) and 4-but-2-ynyloxy-benzenesulfonyl chloride (3.10 g, 12.66 mmol) in H2O-dioxane (40 mL/60 mL) at room temperature. The reaction mixture was stirred for 20 hours at room temperature. The mixture was concentrated and diluted with ethyl acetate. The organic solution was washed with H2O and brine, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (silica, 40% ethyl acetate in hexanes) to give 3.67 g of the title compound as a pale yellow solid. 1H NMR (DMSO-d6): 400 MHz δ 11.05 (s, 1H), 8.31 (d, J=8.8 Hz, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.45 (d, J=1.6 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 7.14 (m, 2H), 6.99 (d, J=8.8 Hz, 2H), 4.80 (q, J=2.4 Hz, 2H), 3.88 (q, J=7.6 Hz, 1H), 3.75 (q, J=7.2 Hz, 2H), 3.00 (dd J=14.4, 7.2 Hz, 1H), 2.88 (dd J=14.4, 7.6 Hz, 1H), 1.82 (t, J=2.4 Hz, 3H), 0.92 (t, J=7.2 Hz, 3H); HRMS: calcd for C23H24BrN2O5S (ESI+, Br79, [M+H]1+), 519.0584; found 519.0589.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washThe organic solution was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica, 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-780d7ad8ed65480da7bd1dbd94ee4bbd
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576222B2

Reaction notes

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