Hydrochloric Acid → HCID 135862883, compound

HRID 2065860Notes

Reaction equation

HRID 2065860 reaction equation
[CH:1]([CH:3]1[CH2:7][S:6][C:5]([CH3:9])(C)[N:4]1C(OC(C)(C)C)=O)=[O:2].Cl.[CH2:18]([C:31](O)=O)[CH2:19]P(CCC(O)=O)CCC(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[OH:40][C:41]1[CH:51]=[CH:50][C:44]2[N:45]=C(C#N)[S:47][C:43]=2[CH:42]=1.[CH:52]([OH:55])([CH3:54])[CH3:53]>O.C1COCC1>[CH:52]([O:55][CH:1]([O:2][CH:18]([CH3:31])[CH3:19])[CH:3]1[CH2:7][S:6][C:5]([C:9]2[S:47][C:43]3[CH:42]=[C:41]([OH:40])[CH:51]=[CH:50][C:44]=3[N:45]=2)=[N:4]1)([CH3:54])[CH3:53]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 119411Tris(2-carboxyethyl)phosphineHCID 98819122-Cyano-6-hydroxybenzothiazoleHCID 20624365HCID 20624365, compound

Product 1

HCID 135862883HCID 135862883, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-formyl-2,2-dimethylthiazolidine-3-carboxylate (750 mg, 3.06 mmol) was suspended in isopropanol (20 mL) and stirred under nitrogen at room temperature. HCl (2.3 mL, 4.0 M dioxane solution) was added dropwise and the reaction was stirred for 16 h. To the reaction mixture a solution of TCEP (1.49 g, 5.2 mmol) in 5 mL water was added. The pH of the reaction was adjusted to ca. 8 with a solution of saturated sodium carbonate. A solution of 6-hydroxy-benzo[d]thiazole-2-carbonitrile (590 mg, 3.35 mmol) in THF (5 mL) was added dropwise and the reaction was stirred for 20 hours. The reaction was stopped when HPLC analysis showed no more progress. The solvent was evaporated in vacuo and the resulting yellow residue was taken up in acetonitrile:water (1:1) and purified by reverse phase chromatography using a 50 mM TEAA/ACN gradient from 90/10 to 100% ACN over 30 minutes. Evaporation of the solvent afforded 300 mgs of the desired product. 1H-NMR (300 MHz, CD2C12) □: 7.94 (d, 1H, J=9 Hz), 7.32 (d, 1H, J=2.4 Hz), 7.05 (dd, 1H, J=8.7 Hz, 2.4 Hz), 4.95 (d, 1H, J=4.5 Hz), 4.79 (1H, m), 3.90 (2H, m), 3.48 (2H, m), 1.2 (12H, m); mass spectrum, calculated for C17H23N2O3S2 (MH+) 367.1. Found 367.2.

Workup

  1. stirringthe reaction was stirred for 16 h
  2. stirringthe reaction was stirred for 20 hours
  3. customThe solvent was evaporated in vacuo
  4. custompurified by reverse phase chromatography
  5. customover 30 minutes
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f097d07694f34403a527043c999821a0
Source dataset
uspto-grants-2012_10
Patent number
US08288559B2

Reaction notes

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