Benzyl chloroformate → HCID 59263930, compound

HRID 644970Notes

Reaction equation

HRID 644970 reaction equation
Br.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[S:12][C:11](=[O:14])[NH:10][C:9]=2[C:8]([OH:15])=[CH:7][CH:6]=1.C(=O)([O-])O.[Na+].[CH3:21][O:22][CH:23]([O:26][CH3:27])[CH:24]=O.C([BH3-])#N.[Na+].Cl[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]>C1COCC1.O.C(OCC)(=O)C.C(O)(=O)C>[CH3:27][O:26][CH:23]([O:22][CH3:21])[CH2:24][N:2]([CH2:3][CH2:4][C:5]1[C:13]2[S:12][C:11](=[O:14])[NH:10][C:9]=2[C:8]([OH:15])=[CH:7][CH:6]=1)[C:33](=[O:34])[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

10

Reactant 5

HCID 10387Benzyl chloroformateHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 516892Sodium Bicarbonate2×HCID 5003444Sodium cyanoborohydrideHCID 138142707-(2-Aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrobromide

Product 1

HCID 59263930HCID 59263930, compoundYield 103.8%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-(2-Aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrobromide (20 g) was dissolved in a mixture of THF (300 ml) and water (150 ml). Sodium hydrogen carbonate (5.77 g) was added and the mixture stirred for 15 min. Acetic acid (7.86 ml) was added, followed by dimethoxyacetaldehyde (14.9 g, 12.91 ml) and the mixture stirred for a further 30 min. Sodium cyanoborohydride (8.64 g) was added portion-wise over 10 min and the solution stirred for a further 20 h. Ethyl acetate (500 ml) and a solution of sodium hydrogen carbonate (17.33 g) in water (250 ml) were added, the mixture was stirred vigorously, benzyl chloroformate (8.78 g, 7.35 ml) was added, and the mixture stirred for 2 h. The organic layer was separated, washed with water, 0.1M aq. HCl, water and brine, dried (anhydrous Na2SO4), filtered and evaporated. The resulting material was purified by flash chromatography on silica using 10% methanol in dichloromethane as eluent to give the sub-title compound as a light brown gum (23.1 g).

Workup

  1. stirringthe mixture stirred for a further 30 min
  2. stirringthe solution stirred for a further 20 h
  3. stirringthe mixture was stirred vigorously
  4. stirringthe mixture stirred for 2 h
  5. customThe organic layer was separated
  6. washwashed with water, 0.1M aq. HCl, water and brine
  7. dry with materialdried (anhydrous Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe resulting material was purified by flash chromatography on silica using 10% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-83964afb997b4d299b6bdce1bdb205d8
Source dataset
uspto-grants-2010_04
Patent number
US07700782B2

Reaction notes

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