Acetic Acid → HCID 59263930, compound

HRID 2234197Notes

Reaction equation

HRID 2234197 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH:4]=O.Cl.[NH2:9][CH2:10][CH2:11][C:12]1[C:20]2[S:19][C:18](=[O:21])[NH:17][C:16]=2[C:15]([OH:22])=[CH:14][CH:13]=1.CC(O)=O.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+].[CH:36]1[CH:41]=[CH:40][C:39]([CH2:42][O:43][C:44](Cl)=[O:45])=[CH:38][CH:37]=1.Cl>C1COCC1.O>[CH3:7][O:6][CH:3]([O:2][CH3:1])[CH2:4][N:9]([CH2:10][CH2:11][C:12]1[C:20]2[S:19][C:18](=[O:21])[NH:17][C:16]=2[C:15]([OH:22])=[CH:14][CH:13]=1)[C:44](=[O:45])[O:43][CH2:42][C:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1

Participants

10

Reactant 7

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochloride

Product 1

HCID 59263930HCID 59263930, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

60% Aqueous dimethoxyacetaldehyde (7.0 ml, 40 mmol) was added dropwise over 1 min to a solution of 7-(2-aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrochloride (10.0 g, 40 mmol) in a mixture of THF (100 ml) and water (50 ml). The reaction was stirred for 30 min, AcOH (2.4 ml, 40 mmol) added, followed by sodium cyanoborohydride (5.1 g, 80 mmol) and stirred for 20 h. The mixture was quenched with water (50 ml), EtOAc (100 ml) added, followed by NaHCO3 (13.6 g, 160 mmol) and the mixture stirred for 15 min. Benzyl chloridocarbonate (6.0 ml, 40 mmol) was then added and the reaction stirred for a further 3 h. The mixture was adjusted to pH7 with 2M HCl, extracted with EtOAc (3×100 ml), washed with water and brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by chromatography on silica with 10% (0.1% aqNH3/MeOH)/DCM as eluant to give the sub-title compound as a colourless oil. Yield (6.0 g).

Workup

  1. stirringstirred for 20 h
  2. customThe mixture was quenched with water (50 ml), EtOAc (100 ml)
  3. additionadded
  4. stirringthe mixture stirred for 15 min
  5. stirringthe reaction stirred for a further 3 h
  6. extractionextracted with EtOAc (3×100 ml)
  7. washwashed with water and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customThe residue was purified by chromatography on silica with 10% (0.1% aqNH3/MeOH)/DCM as eluant

Sources & evidence

ORD record
ord-d081a938ef2041f59465f476b70dbab7
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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