Benzyl chloroformate → HCID 86707924, compound

HRID 595370Notes

Reaction equation

HRID 595370 reaction equation
[OH:1][CH2:2][C@H:3]1[O:11][C@H:10]2[C@H:6]([N:7]=[C:8]([NH:12][CH3:13])[S:9]2)[C@@H:5]([OH:14])[C@@H:4]1[OH:15].C([O-])(O)=O.[Na+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C1COCC1.O>[OH:15][C@@H:4]1[C@@H:3]([CH2:2][OH:1])[O:11][C@H:10]2[C@H:6]([N:7]=[C:8]([N:12]([CH3:13])[C:22](=[O:23])[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[S:9]2)[C@H:5]1[OH:14]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 67205978HCID 67205978, compound

Product 1

HCID 86707924HCID 86707924, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a suspension of -(3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (1.50 g, 6.40 mmol) and NaHCO3 (1.01 g, 12.0 mmol) in THF/water (40 mL, 1:3) was added benzyl chloroformate (1.70 g, 10.0 mmol). The mixture was stirred at room temperature for 4 days. The organic solvent was removed under reduced pressure to result in a precipitate. The precipitated solid was collected by filtration, washed with Et2O and dried under vacuum, affording benzyl (-(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate as a white solid (1.72 g, 73%). 1H NMR (400 MHz, CD3OD) δ 7.44-7.32 (m, 5H), 6.13 (d, J=6.9 Hz, 1H), 5.27-5.20 (m, 2H), 4.14 (t, J=6.1 Hz, 1H), 4.02 (t, J=4.9 Hz, 1H), 3.74 (dd, J=2.4, 12.0 Hz, 1H), 3.63 (dd, J=6.1, 12.0 Hz, 1H), 3.53 (dd, J=4.5, 9.2 Hz, 1H), 3.47-3.43 (m, 1H), 3.39 (s, 3H).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. customto result in a precipitate
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with Et2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b11167f5cc1f4227ae8a35d726ffdaa5
Source dataset
uspto-grants-2016_01
Patent number
US09243020B2

Reaction notes

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