Methyl chloroformate → HCID 66551947, compound

HRID 1422546Notes

Reaction equation

HRID 1422546 reaction equation
[NH2:1][C:2]1[S:3][C@H:4]2[O:10][C@H:9]([CH2:11][OH:12])[C@@H:8]([OH:13])[C@H:7]([OH:14])[C@H:5]2[N:6]=1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:22]([O:24][CH3:25])=[O:23]>C1COCC1.O.CO.C(Cl)Cl>[CH3:25][O:24][C:22](=[O:23])[NH:1][C:2]1[S:3][C@H:4]2[O:10][C@H:9]([CH2:11][OH:12])[C@@H:8]([OH:13])[C@H:7]([OH:14])[C@H:5]2[N:6]=1

Participants

8

Reactant 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 67204778HCID 67204778, compound

Product 1

HCID 66551947HCID 66551947, compoundYield 72.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3aR,5R,6S,7R,7aR)-2-amino-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (220 mg, 1.00 mmol) and Na2CO3 (212 mg, 2.00 mmol) in THF (10 mL) and water (10 mL) was added methyl chloroformate (0.08 mL, 1.1 mmol) at 0° C. After stirred for 2 h, the reaction mixture was condensed to give a residue, which was dissolved in MeOH (8 mL) and DCM (20 mL). After filtration the solution was concentrated under vacuum to give a residue, which was purified by Prep-HPLC with the following conditions [(Agilent 1200 Detect prep HPLC): Column, SunFire Prep C18; mobile phase, Water with 0.03% ammonia and CH3CN (10% CH3CN up to 45% in 10 min); Detector, UV 220 nm.] to give the title compound as a white solid (201 mg,72%). (ES, m/z)[M+H]+279.0; 1H NMR (300 MHz, D2O) δ6.46-6.49 (d, J=6.9 Hz, 1H), 4.25-4.29 (dd, J=6.6 Hz, 6.9 Hz, 1H), 3.95-3.99 (dd, J=6.0 Hz, 6.3 Hz, 1H), 3.74-3.78 (m, 1H), 3.74 (s, 3H), 3.51-3.68 (m, 3H).

Workup

  1. customcondensed
  2. customto give a residue, which
  3. filtrationAfter filtration the solution
  4. concentrationwas concentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by Prep-HPLC with the following conditions [(Agilent 1200 Detect prep HPLC)
  7. waitmobile phase, Water with 0.03% ammonia and CH3CN (10% CH3CN up to 45% in 10 min)

Sources & evidence

ORD record
ord-b76b7023ac81429793c258062a50843e
Source dataset
uspto-grants-2015_01
Patent number
US08927507B2

Reaction notes

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