Hydroxide → HCID 18687871, compound

HRID 1873207Notes

Reaction equation

HRID 1873207 reaction equation
[Br:1][C:2]1[CH:20]=[C:19]([C:21]2[C:30]3[C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[S:33][C:29]=3[C:28]([O:38][CH2:39][C:40]([OH:42])=[O:41])=[C:27]3[C:22]=2[CH:23]=[CH:24][CH:25]=[CH:26]3)[CH:18]=[C:17]([Br:43])[C:3]=1[O:4][C@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8]C)=[O:7].[OH-]>O1CCCC1.CO>[Br:1][C:2]1[CH:20]=[C:19]([C:21]2[C:30]3[C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[S:33][C:29]=3[C:28]([O:38][CH2:39][C:40]([OH:42])=[O:41])=[C:27]3[C:22]=2[CH:23]=[CH:24][CH:25]=[CH:26]3)[CH:18]=[C:17]([Br:43])[C:3]=1[O:4][CH:5]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 961HydroxideHCID 86755713HCID 86755713, compound

Product 1

HCID 18687871HCID 18687871, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-[2,6-dibromo-4-(6-carboxymethoxy-benzo [b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-3-phenyl-propionic acid, methyl ester (0.436 g, 0.594 mmol) in tetrahydrofuran (9 mL) and methanol (3 mL) was added an aqueous solution of potassuim hydroxide (1 N, 2.37 mL, 2.37 mmol, 4 eq) dropwise at room temperature. After stirring 3.5 hours the solvents were removed and the residue was combined with water. The suspension was acidified with 10% aqueous hydrochloric acid and diethyl ether was added. The biphasic mixture was shaken well before the layers were separated. The organic phase was washed with water and concentrated. The residue was triturated with petroleum ether and dried in vacuo to provide the title compound as a white solid (0.366 g, 87%): mp 110-120° C.; [a]25/D =+49.620 (10.076 mg/mL, methanol); NMR (DMSO-d6): δ13.21 (broad s, 2 H), 8.40 (d, J=8 Hz, 1H), 8.03 (d, J=8 Hz, 1H), 7.74 (dd, J=2, 8 Hz, 2 H), 7.68 (ddd, J=8, 7, 1 Hz, 1 H), 7.57 (ddd, J=8, 7, 1 Hz, 1H), 7.52 - 7.45 (m, 2 H), 7.43 - 7.38 (m, 2 H), 7.37 -7.11 (m, 2 H), 7.10-7.20 (m, 2 H), 6.69 (d, J=8Hz, 1H), 5.30 (t, J=7 Hz, 1 H), 4.90 (s, 2 H), 3.41 (d, J=7 Hz, 2 H); MS (+FAB): [M+], 2 bromine isotope pattern, 704 (9%), 706 (22%), 708 (22%); Anal. Calc. for C33212Br2O6S: C, 56.11, H, 3.14, N, 0.00. Found: C, 55.93, H, 3.28, N, 0.09.

Workup

  1. customwere removed
  2. additionwas added
  3. stirringThe biphasic mixture was shaken well before the layers
  4. customwere separated
  5. washThe organic phase was washed with water
  6. concentrationconcentrated
  7. customThe residue was triturated with petroleum ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-94126fe0497f4bae9e24a780de7ca7dd
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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