Hydrochloric Acid → HCID 54018908, compound

HRID 1637121Notes

Reaction equation

HRID 1637121 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:16][C:17]3[S:18][CH:19]([CH3:23])[CH:20](O)[N:21]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CCOCC>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:24]#[C:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:16][C:17]3[S:18][C:19]([CH3:23])=[CH:20][N:21]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54536844HCID 54536844, compound

Product 1

HCID 54018908HCID 54018908, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (+/-)-2-[2-(3-cyclopentyloxy-4-methoxyphenyl)-4-phenylbut-3-ynyl]-4-hydroxy-5-methyl-4,5-dihydrothiazole (70 mg, 0.2 mmol) in CDCl3 (4 ml) was treated with HCl (0.2 ml of a 1N solution in Et2O) and heated to 50° for 3 hr. The solvent was evaporated, the residue taken up in Et2O, washed with aqueous NaHCO3, H2O, dried and the solvent evaporated. Purification by flash chromatography (silica gel, 2% Et2O in CH2Cl2) gave the titled compound (19 mg, 28%). 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.36 (s, 1 H), 7.30 (m, 3 H), 7.00 (m, 1 H), 6.92 (d, 1 H), 6.84 (d, 1 H), 4.74 (m, 1 H), 4.28 (t, 1 H), 3.82 (s, 3 H), 3.40 (d, 2 H), 2.42 (s, 3 H), 1.78-1.98 (m, 6 H), 1.60 (m, 2 H).

Workup

  1. temperatureheated to 50° for 3 hr
  2. customThe solvent was evaporated
  3. washwashed with aqueous NaHCO3, H2O
  4. customdried
  5. customthe solvent evaporated
  6. customPurification by flash chromatography (silica gel, 2% Et2O in CH2Cl2)

Sources & evidence

ORD record
ord-d328250cc60f41478129aa3436b43c37
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

Loading…