Methanol → HCID 9918000, compound

HRID 1278806Notes

Reaction equation

HRID 1278806 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:39])[C@H:6]([O:14][C:15]1[C:20]([Br:21])=[CH:19][C:18]([C:22]2[C:34]3[C:33]([CH3:35])=[C:32]([CH3:36])[S:31][C:30]=3[C:29]([Br:37])=[C:28]3[C:23]=2[CH:24]=[CH:25][CH:26]=[CH:27]3)=[CH:17][C:16]=1[Br:38])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO>C1COCC1>[Br:21][C:20]1[CH:19]=[C:18]([C:22]2[C:34]3[C:33]([CH3:35])=[C:32]([CH3:36])[S:31][C:30]=3[C:29]([Br:37])=[C:28]3[C:23]=2[CH:24]=[CH:25][CH:26]=[CH:27]3)[CH:17]=[C:16]([Br:38])[C:15]=1[O:14][C@H:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:5]([OH:39])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 10169000HCID 10169000, compound

Product 1

HCID 9918000HCID 9918000, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous potassium hydroxide (1 N, 2.00 mL, 2.00 mmol) was added to a stirred solution of (R)-2-[2,6-dibromo-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenoxy]3-phenyl-propionic acid methyl ester (0.699 g, 0.99 mmol) in THF (12 mL)/methanol (7mL). After 3 h the solution was concentrated, diluted with water (100 mL) and acidified with 10% aqueous HCl. The solid was filtered, washed with water and triturated with petroleum ether and dried in vacuo to provide the title compound as a white solid (0.645 g, 94%): [a]D25=+14.29° (8.75 mg(m CHCl3); NMR (DMSO-d6); δ 8.19 (d, J=8 Hz, 1H), 7.66 (ddd, J=8, 7, 1 Hz, 1H), 7.61 (s, 2H), 7.52 (ddd, J=8, 7, 1 Hz, 1H), 7.41 (d, J=8 Hz, 1H), 7.38-7.20 (m, 5H), 5.27 (t, J 7 Hz, 1H), 3.37 (dd, 14, 6 Hz, 1H), 3.28 (dd, 14, 7 Hz, 1H), 2.43 (s, 3H), 1.59 (s,3H); MS (+FAB): 3 bromine isotope pattern 686 (20%), 688 (75%), 690 (75%), 692 (25%); Anal. Calc. for C29H21Br3O3S: C, 50,53, H, 3.07, N, 0.00. Found: C, 50.04, H, 3.11, N, 0.05.

Workup

  1. concentrationAfter 3 h the solution was concentrated
  2. additiondiluted with water (100 mL)
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customtriturated with petroleum ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-505488eeeea84bdd8fb11cb1261ec33b
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

Loading…