Hydrochloric Acid → 3-(5-bromo-1H-indol-3-yl)-2-(4-but-2-ynyloxy-benzenesulfonyl amino)-propionic acid

HRID 2104215Notes

Reaction equation

HRID 2104215 reaction equation
C([O:3][C:4](=[O:32])[CH:5]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]#[C:30][CH3:31])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[NH:9][CH:8]=1)C.CO.[OH-].[Na+].Cl>O1CCCC1>[Br:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:6][CH:5]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]#[C:30][CH3:31])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:4]([OH:32])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 578059912-(4-but-2-ynyloxy-benzenesulfonylamino)-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl ester

Product 1

HCID 115912683-(5-bromo-1H-indol-3-yl)-2-(4-but-2-ynyloxy-benzenesulfonyl amino)-propionic acidYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-But-2-ynyloxy-benzenesulfonylamino)-3-(5-bromo-1H-indol-3-yl)-propionic acid ethyl ester (0.100 g, 0.193 mmol) was dissolved in 0.5 mL tetrahydrofuran. To the solution was added MeOH (0.5 mL) and 1 N NaOH (0.4 mL, 0.4 mmol). The reaction mixture was placed in a shaker for 10 hours at room temperature. The solution was acidified with 1N HCl and extracted with ethyl acetate (3×3 mL). The organic solution was concentrated and the residue was purified by RP-HPLC to give 0.089 g (94%) of the title compound as a pale yellow solid. 1H NMR (DMSO-d6): 400 MHz δ 12.65 (bs, 1H), 11.01 (s, 1H), 8.08 (d, J=8.8 Hz, 1H), 7.48 (m, 3H), 7.26 (d, J=8.8 Hz, 1H), 7.13 (m, 2H), 6.89 (d, J=9.2 Hz, 2H), 4.77 (q, J=2.8 Hz, 2H), 3.82 (q, J=8.4 Hz, 1H), 3.01 (dd J=14.6, 6.4 Hz, 1H), 2.82 (dd J=14.6, 8.0 Hz, 1H), 1.83 (t, J=2.4 Hz, 3H); HRMS: calcd for C21H20BrN2O5S (ESI+, Br79, [M+H]1+), 491.0271; found 491.0287; LCMS m/z (ESI) [M−H] 489 (Br79), retention time=2.75 min.

Workup

  1. extractionextracted with ethyl acetate (3×3 mL)
  2. concentrationThe organic solution was concentrated
  3. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-ab3420d4070f42c9ae894a984bc85c12
Source dataset
uspto-grants-2009_08
Patent number
US07576222B2

Reaction notes

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