HCID 86701110, compound → HCID 86701112, compound

HRID 1396260Notes

Reaction equation

HRID 1396260 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]=[O:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH2:28][CH2:29][F:30])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[S:14]2)[C@H:10]1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39][Mg]Cl>C1COCC1>[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]([OH:19])[CH3:39])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH2:28][CH2:29][F:30])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[S:14]2)[C@H:10]1[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 86701110HCID 86701110, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 86701112HCID 86701112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of tert-butyl (3aR,5S,6S,7R,7aR)-6,7-bis(benzyloxy)-5-formyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate (400 mg, 0.73 mmol) in THF (20 mL) was added methylmagnesium chloride (1 mL, 3M in THF). After stirred for 3 hours at 0-5°C., the resulting solution was quenched with saturated aqueous NH4Cl (10 mL) and extracted with ethyl acetate (3×30 mL). The organic layers were dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 20% ethyl acetate in petroleum ether to give compound 73 as a yellow oil (0.37 g, 90%, diasteromers' ratio is 1:4). (ES, m/z) [M+H]+ 561.0; 1H NMR (300 MHz, CDCl3) δ 7.25-7.44 (m, 10H), 6.13-6.15 (d, J=6.9 Hz, 1H), 4.73-4.78 (m, 2H), 4.54-4.68 (m, 2H), 4.28-4.49 (m, 4H), 4.07-4.25 (m, 2H), 3.75-3.97 (m, 2H), 3.12-3.17 (m, 1H), 1.54 (s, 9H), 1.22-1.24 (d, J=6.3 Hz, 3H).

Workup

  1. customthe resulting solution was quenched with saturated aqueous NH4Cl (10 mL)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by a silica gel column
  7. washeluting with 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-c898a3df5a044e9493a2f6e1c9bc7a02
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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