Benzyl chloroformate → HCID 59263886, compound

HRID 644971Notes

Reaction equation

HRID 644971 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+].O=[CH:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C([BH3-])#N.[Na+].Cl[C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38]>C1COCC1.O.C(OCC)(=O)C.C(O)(=O)C>[C:27]([O:26][C:25]([NH:24][CH2:23][CH2:22][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:37](=[O:38])[O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:31])([CH3:30])([CH3:29])[CH3:28]

Participants

10

Reactant 5

HCID 10387Benzyl chloroformate2×HCID 516892Sodium Bicarbonate2×HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 138142707-(2-Aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrobromide

Product 1

HCID 59263886HCID 59263886, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

7-(2-Aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrobromide (3.66 g) was suspended in a mixture of THF (50 ml) and water (25 ml). Sodium hydrogen carbonate (1.06 g) was added and the mixture stirred for 15 min. Acetic acid (1.44 ml) was added, followed by a solution of tert-butyl (2-oxoethyl)carbamate (2.0 g) in THF (10 ml), and the mixture stirred for a further 30 min. Sodium cyanoborohydride (1.58 g) was added and the solution stirred for a further 18 h. Ethyl acetate (100 ml) and a solution of sodium hydrogen carbonate (3.17 g) in water (50 ml) were added, the mixture was stirred vigorously, benzyl chloroformate (709 ul) was added, and the mixture stirred for 15 min. A second portion of benzyl chloroformate (170 ul) was added and the mixture stirred for a further 30 min. The reaction mixture was extracted with ethyl acetate (×2) and filtered through celite. The organic extracts were combined, washed with water, dried (anhydrous Na2SO4), filtered and evaporated. The resulting material was purified by flash chromatography on silica using isohexane:ethyl acetate (50:50, 25:75, 100%) as eluent to give the sub-title compound (2.94 g).

Workup

  1. stirringthe mixture stirred for a further 30 min
  2. stirringthe solution stirred for a further 18 h
  3. stirringthe mixture was stirred vigorously
  4. stirringthe mixture stirred for 15 min
  5. stirringthe mixture stirred for a further 30 min
  6. extractionThe reaction mixture was extracted with ethyl acetate (×2)
  7. filtrationfiltered through celite
  8. washwashed with water
  9. dry with materialdried (anhydrous Na2SO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe resulting material was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-f581b5316d814a72bc3887d977216bb3
Source dataset
uspto-grants-2010_04
Patent number
US07700782B2

Reaction notes

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