Sodium → HCID 59486077, compound

HRID 1972277Notes

Reaction equation

HRID 1972277 reaction equation
CS(O[CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C@H:8]1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)(=O)=O.[NH:28]1[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N:31][N:30]=[N:29]1.[Na]>CN(C=O)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([N:9]2[C@@H:8]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[C@H:7]([CH2:6][N:29]3[N:30]=[N:31][C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[N:28]3)[O:11][C:10]2=[O:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 59485584HCID 59485584, compoundHCID 178470518HCID 178470518, compound

Product 1

HCID 59486077HCID 59486077, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A small reaction tube fitted with a screw cap is charged with ((4S,5R)-3-(4-chlorophenyl)-4-(3-methoxyphenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate (50 mg, 0.12 mmol) and DMF (1 mL). Ethyl 1H-tetrazole-5-carboxylate, sodium salt (39 mg, 0.24 mmol) is added and the mixture is heated to 70° C. overnight. The cooled reaction is quenched with water, extracted with EtOAc, combined organics are washed with brine, dried over MgSO4, filtered, concentrated, and purified by flash chromatography (12 g Redisep cartridge, 30-50% EtOAc/hexanes) to give the title compound. 1H NMR (acetone-d6, 400 MHz) δ 7.53-7.43 (m, 2H), 7.34-7.28 (m, 3H), 7.10-7.08 (m, 1H), 7.06-7.00 (m, 2H), 6.92-6.90 (m, 1H), 5.67 (d, J=5.3 Hz, 1H), 5.52 (dd, J=(ddd, J=14.6, 6.5 Hz, 1H), 5.47-5.41 (m, 1H), 5.11-4.99 (m, 1H), 4.46-4.41 (m, 2H), 3.76 (s, 3H), 1.39-1.35 (m, 3H); HPLC-MS calculated C21H20ClN5O5 (M+H+) 458.1, found 458.1.

Workup

  1. customA small reaction tube fitted with a screw
  2. customcap
  3. customThe cooled reaction
  4. customis quenched with water
  5. extractionextracted with EtOAc
  6. washcombined organics are washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography (12 g Redisep cartridge, 30-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a72418da1f064e2fa85da2a344a83676
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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