Potassium Hydroxide → HCID 10283354, compound

HRID 1278820Notes

Reaction equation

HRID 1278820 reaction equation
C[O:2][C:3](=[O:41])[C@H:4]([O:12][C:13]1[C:18]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:17][C:16]([C:24]2[C:36]3[C:35]([CH3:37])=[C:34]([CH3:38])[S:33][C:32]=3[C:31]([Br:39])=[C:30]3[C:25]=2[CH:26]=[CH:27][CH:28]=[CH:29]3)=[CH:15][C:14]=1[Br:40])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[K+]>O1CCCC1.CO>[Br:40][C:14]1[CH:15]=[C:16]([C:24]2[C:36]3[C:35]([CH3:37])=[C:34]([CH3:38])[S:33][C:32]=3[C:31]([Br:39])=[C:30]3[C:25]=2[CH:26]=[CH:27][CH:28]=[CH:29]3)[CH:17]=[C:18]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:13]=1[O:12][C@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:41])=[O:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54329283HCID 54329283, compound

Product 1

HCID 10283354HCID 10283354, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-[2-bromo-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-6-cyclopentyl-phenoxy]-3-phenyl-propionic acid methyl ester (1.0 g, 1.5 mmol) in tetrahydrofuran (30 mL) and methanol (10 mL) at room temperature was added dropwise aqueous potassium hydroxide (3.0 mL of a 1 N solution, 3.0 mmol). After 4 h the reaction mixture was concentrated under reduced pressure. The residue was taken up in water (100 mL) and acidified with aqueous 10% hydrochloric acid. After stirring for 15 min the solid was filtered and washed with water:methanol (95:5). The solid was dried under a vacuum at 50° C. for 18 h to yield the title compound as a white solid (0.99 g, 100%): Opt. Rot. [a]25/D=+38.44° (9.624 mg/mL, MeOH); NMR (DMSO-d6): δ 13.01 (broad s, 1H), 8.19 (d, 1H), 7.67-7.62 (m, 1H), 7.54-7.22 (m, 9H), 4.92 (m, 1H), 3.46 (m, 1H), 3.34 (m, 2H), 2.42 and 2.41 (two singlets, 3H, rotational isomers), 1.99 (m, 1H), 1.98 (m, 1H), 1.72-1.27 (m containing two s at δ 1.57 and 1.53 (rotational isomers), 6H); MS(−ESI): [M−H], 2 bromine isotope pattern, 675 (72%), 677 (100%), 679 (66%); Anal. Calc. for C34H30Br2O3S: C, 60.19, H, 4.46, N, 0.00. Found: C, 59.53, H, 4.35, N, −0.04.

Workup

  1. concentrationAfter 4 h the reaction mixture was concentrated under reduced pressure
  2. filtrationwas filtered
  3. washwashed with water:methanol (95:5)
  4. customThe solid was dried under a vacuum at 50° C. for 18 h

Sources & evidence

ORD record
ord-fcf122408eaf46efbc89ef87b2d5ecb1
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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