1,2-Dichloroethane → HCID 68493244, compound

HRID 42542Notes

Reaction equation

HRID 42542 reaction equation
C(O)(=O)C1C=CC=CC=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C.[C:31]([NH:39][C@@H:40]1[CH2:45][CH2:44][O:43][CH2:42][C@@H:41]1[C:46]([O:48][CH3:49])=[O:47])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[C:31]([NH:39][C@H:40]1[CH2:45][CH2:44][O:43][CH2:42][C@H:41]1[C:46]([O:48][CH3:49])=[O:47])(=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 59474987HCID 59474987, compound

Product 1

HCID 68493244HCID 68493244, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (3S,4S)- and (3R,4R)-methyl 4-aminotetrahydro-2H-pyran-3-carboxylate, HBr (prepared in a similar manner as described in International Patent application No. WO 2003/024899, 500 mg, 2.083 mmol), benzoic acid (254 mg, 2.083 mmol), HOBt (383 mg, 2.499 mmol), EDC (479 mg, 2.499 mmol) and triethylamine (0.581 mL, 4.17 mmol) were mixed in methylene chloride (10 mL) at 25° C. and stirred for 20 hours. At the conclusion of this period, the reaction was worked up by adding methylene chloride and then rinsing the mixture with saturated sodium carbonate (1×). The methylene chloride layer was dried over sodium sulfate and concentrated to give an off-white solid. The off-white solid was purified over silica gel in 3:1 to 1:1 hexanes/EtOAc to 100% EtOAc to yield a mixture of (3R,4R)-methyl 4-benzamidotetrahydro-2H-pyran-3-carboxylate and (3S,4S)-methyl 4-benzamidotetrahydro-2H-pyran-3-carboxylate (500 mg, 1.899 mmol, 91% yield) as a white solid. MS (ESI+)=264.24 (M+H)+.

Workup

  1. customprepared in a similar manner
  2. washrinsing the mixture with saturated sodium carbonate (1×)
  3. dry with materialThe methylene chloride layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give an off-white solid
  6. customThe off-white solid was purified over silica gel in 3:1 to 1:1 hexanes/EtOAc to 100% EtOAc
  7. customto yield

Sources & evidence

ORD record
ord-94c1f4f601c64081b36b50a962a958bc
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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