Triethylamine → HCID 11676244, compound

HRID 2104207Notes

Reaction equation

HRID 2104207 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:23]=[C:22]2[C:12]([NH:13][CH:14]=[C:15]2[CH2:16][CH:17]([C:19]([OH:21])=[O:20])[NH2:18])=[CH:11][CH:10]=1.[CH2:24]([O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)[C:25]#[C:26][CH3:27]>O.O1CCOCC1>[CH2:24]([O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:18][CH:17]([CH2:16][C:15]2[C:22]3[C:12](=[CH:11][CH:10]=[C:9]([CH3:8])[CH:23]=3)[NH:13][CH:14]=2)[C:19]([OH:21])=[O:20])(=[O:37])=[O:36])=[CH:31][CH:30]=1)[C:25]#[C:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 928525-Methyl-DL-tryptophanHCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 11676244HCID 11676244, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Triethylamine (0.38 mL, 2.75 mmol) was added to a solution of 5-methyl-DL-tryptophan (0.20 g, 0.92 mmol) and 4-but-2-ynyloxy-benzenesulfonyl chloride (0.25 g, 1.01 mmol) in H2O-dioxane (1.6 mL/2.4 mL) at room temperature. The reaction mixture was stirred for 20 hours at room temperature. The mixture was then concentrated and acidified with HCl. The mixture was extracted with ethyl acetate (3×10 mL). The organic solution was washed with H2O and brine, dried over Na2SO4, and concentrated. The residue was purified by RP-HPLC to give 0.32 g (81%) of the title compound as a pale yellow solid. Mp=45-46° C.; 1H NMR (DMSO-d6): 400 MHz δ 12.54 (bs, 1H), 10.64 (s, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.53 (m, 2H), 7.17 (d, J=8.0 Hz, 1H), 7.00 (m, 2H), 6.95 (m, 2H), 6.86 (dd J=8.0, 4.0 Hz, 1H), 4.78 (q, J=2.4 Hz, 2H), 3.81 (q, J=7.6 Hz, 1H), 3.00 (dd J=14.4, 6.8 Hz, 1H), 2.79 (dd J=14.4, 7.8 Hz, 1H), 2.33 (s, 3H), 1.82 (t, J=2.4 Hz, 3H); HRMS: calcd for C22H23N2O5S (ESI+, [M+H]1+), 427.1322; found 427.1327; LCMS m/z (ESI) [M+H]1+ 427, retention time=2.69 min.

Workup

  1. concentrationThe mixture was then concentrated
  2. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  3. washThe organic solution was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-bfe43b6483c74e4980b6050a576524fa
Source dataset
uspto-grants-2009_08
Patent number
US07576222B2

Reaction notes

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