Hydrochloric Acid → 2-Methyl-4-(6-carboxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole

HRID 972243Notes

Reaction equation

HRID 972243 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[S:5][C:6](/[CH:18]=[CH:19]/[C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[N:8]=1.Cl>O.C(O)(C)C>[CH3:3][C:4]1[S:5][C:6](/[CH:18]=[CH:19]/[CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 214064272-Methyl-4-(6-carboxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole

Product 1

HCID 214064282-Methyl-4-(6-carboxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazoleYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

The solution of 76 mg of sodium borohydride in 6 ml of water was added to the solution of 351 mg of 2-methyl-4-(6-carboxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole (Ib, R1 = CH3) in 4 ml of isopropanol. The reaction mixture was allowed to stand overnight at room temperature, then diluted with 50 ml of water, acidified with 1 N hydrochloric acid and extracted with 3 × 25 ml of ethyl acetate. The ethyl acetate extract was dried over sodium sulphate and evaporated in vacuo. The obtained 317 mg of evaporation residue was purified by preparative thin layer chromatography in the way specified in Example 6. Thus, 245 mg of 2-methyl-4-(6-carboxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole (Id, R1 = CH3) were obtained. IR spectrum (film): ν OH 3500-2300, ν CH 3000-2860, ν C=O 1710, ν C=C 1640 cm -1.

Workup

  1. extractionextracted with 3 × 25 ml of ethyl acetate
  2. extractionThe ethyl acetate extract
  3. dry with materialwas dried over sodium sulphate
  4. customevaporated in vacuo
  5. customThe obtained 317 mg of evaporation residue
  6. customwas purified by preparative thin layer chromatography in the way

Sources & evidence

ORD record
ord-2d4cbee735554e8f85ad51ab3e70fb24
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

Loading…