Hydrochloric Acid → HCID 57520941, compound

HRID 595374Notes

Reaction equation

HRID 595374 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19](C)[C:20](=O)OC(C)(C)C)[S:16]2)[C@H:12]([F:28])[C@@H:11]1[OH:29])(C(C)(C)C)(C)C.Cl>CO>[F:28][C@H:12]1[C@H:13]2[N:14]=[C:15]([NH:19][CH3:20])[S:16][C@H:17]2[O:18][C@H:10]([CH2:9][OH:8])[C@H:11]1[OH:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86707926HCID 86707926, compound

Product 1

HCID 57520941HCID 57520941, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (-(3aR,5R,6R,7S,7aR)-5-(((tert-butyldimethylsilyl)oxy)methyl)-7-fluoro-6-hydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.200 g, 0.444 mmol) in dry MeOH (6 mL) was bubbled HCl gas for 30 sec. The mixture was stirred at room temperature for 5 h. After the solvent was evaporated under reduced pressure, the residue was neutralized with 1.0 M NH3 in MeOH and purified on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:8) followed by recrystallization from MeOH/Et2O, affording -(3aR,5R,6R,7S,7aR)-7-fluoro-5-(hydroxymethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-6-ol as a white solid (0.093 g, 89%). 1H NMR (400 MHz, CD3OD) δ 6.62 (d, J=6.5 Hz, 1H), 4.89 (td, J=3.5 Hz, 51.0 Hz, 1H), 4.54 (ddd, J=3.5, 6.5, 20.6, 1H), 3.98-3.94 (m, 1H), 3.90-3.84 (m, 1H), 3.83-3.81 (m, 1H), 3.75 (dd, J=5.4, 12.2 Hz, 1H), 2.99 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 90.63 (d, J=181.3 Hz), 88.53 (d, J=2.3 Hz), 73.60 (d, J=4.3 Hz), 66.02 (d, J=17.3 Hz), 64.80-64.50 (m), 62.44, 31.38; MS, (ES, m/z) [M+H]+ 237.1.

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. custompurified on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:8)
  3. customfollowed by recrystallization from MeOH/Et2O

Sources & evidence

ORD record
ord-26ac9d81733b4073b114df40672a825a
Source dataset
uspto-grants-2016_01
Patent number
US09243020B2

Reaction notes

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