Water → HCID 21970367, compound

HRID 1873189Notes

Reaction equation

HRID 1873189 reaction equation
[Br:1][C:2]1[CH:18]=[C:17]([C:19]2[C:28]3[C:29]4[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=4[S:31][C:27]=3[C:26]([Br:36])=[C:25]3[C:20]=2[CH:21]=[CH:22][CH:23]=[CH:24]3)[CH:16]=[C:15]([Br:37])[C:3]=1[O:4][C@H:5]([CH2:10][C:11]([O:13]C)=[O:12])[C:6]([O:8]C)=[O:7].O>Cl.O1CCOCC1>[Br:1][C:2]1[CH:18]=[C:17]([C:19]2[C:28]3[C:29]4[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=4[S:31][C:27]=3[C:26]([Br:36])=[C:25]3[C:20]=2[CH:21]=[CH:22][CH:23]=[CH:24]3)[CH:16]=[C:15]([Br:37])[C:3]=1[O:4][C@H:5]([CH2:10][C:11]([OH:13])=[O:12])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 962WaterHCID 54401288HCID 54401288, compound

Product 1

HCID 21970367HCID 21970367, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of (R)-2-[2,6-Dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d ]thiophen-11-yl)-phenoxy]-succinic acid, dimethly ester (0.317 g, 0.448 mmol) in 4M HCl in dioxane (5 mL) was combined with water (5 mL) and concentrated HCl (1 mL) in a sealed pressure bottle and heated for 9 hours. After remaining at ambient temperature for an additional 14 hours the reaction mixture was partitioned between water and ether. The layers were separated and acid treated silica gel (7 mL) was added to the ether layer. The solvent was removed and the adsorbate was purified by flash chromatography (acid treated silica gel, eluant 80:20 pet. ether:ethyl acetate) to provide the title compound as a white solid (0.142 g, 47%), mp 163-164° C.; [a]D25=+14.16° (8.825 mg/mL, methanol); NMR (DMSO-d6); δ13.6 - 13.2 (broad singlet, 1 H,), 12.7 - 12.6 (broad singlet, 1 H), 8.28 (d, J=8 Hz, 1 H), 8.07 (d, J=8 Hz, 1 H), 7.82 - 7.78(m, 3 H), 7.65 - 7.57(m, 2 H,), 7.52(dd, J=7, 1 Hz, 1 H), 7.31(dd, J=7, 1, 1H), 6.70(d, J=8 Hz, 1 H), 5.32 (t, J=8 Hz), 3.67(m, 2 H); MS (-FAB) [M-H]-; 3 bromine pattern detected, 675(25%), 677(10%), 679(25%), 681(10%); Anal. Calc. for C26H15Br3O5S: C, 45.78, H, 2.23, N, 0.00. Found: C, 46.42, H, 2.40, N, 0.05.

Workup

  1. temperatureheated for 9 hours
  2. customthe reaction mixture was partitioned between water and ether
  3. customThe layers were separated
  4. additionacid treated silica gel (7 mL)
  5. additionwas added to the ether layer
  6. customThe solvent was removed
  7. customthe adsorbate was purified by flash chromatography (acid treated silica gel, eluant 80:20 pet. ether:ethyl acetate)

Sources & evidence

ORD record
ord-ca1ed008ee7444c290a1f8418b934b6c
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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