Sodium Carbonate → HCID 117698088, compound

HRID 1778559Notes

Reaction equation

HRID 1778559 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][CH:9]2[NH:11][CH:6]1[CH2:7][C@H:8]2[C:12]([O:14][CH2:15]C)=[O:13])(=[O:3])[CH3:2].O=C1CC2(C(OC)=O)N(C(OC(C)(C)C)=O)C1CC2.C(N[C@H]1[C@H](C(OC)=O)CC=CC1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[C:56](Cl)([O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=[O:57]>C(Cl)Cl.O>[C:1]([O:4][CH:5]1[CH2:10][CH:9]2[N:11]([C:56]([O:58][CH2:59][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[O:57])[CH:6]1[CH2:7][CH:8]2[C:12]([O:14][CH3:15])=[O:13])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 216369877-tert-Butyl 1-methyl 3-oxo-7-azabicyclo[2.2.1]heptane-1,7-dicarboxylateHCID 117700402HCID 117700402, compoundHCID 131734831HCID 131734831, compound

Product 1

HCID 117698088HCID 117698088, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl (5R)-2-acetoxy-7-azabicyclo[2.2.1]heptane-5-carboxylate 151b (prepared in analogy to O7-tert-butyl O4-methyl 2-oxo-7-azabicyclo[2.2.1]heptane-4,7-dicarboxylate starting from methyl trans-6-acetamidocyclohex-3-ene-1-carboxylate with procedures reported in the literature: Org. Lett., Vol. 9, No. 7, 2007 p 1235-p 1238) (0.55 g, 2.4 mmol) in DCM (10 mL) and sodium carbonate (0.76 g, 7.2 mmol) in water (3 mL) was added CbzCl (0.61 g, 3.6 mmol) dropwise. After addition, the mixture was stirred for 2 hours, then extracted with DCM. Removal of solvent afforded O7-benzyl O5-methyl 2-acetoxy-7-azabicyclo[2.2.1]heptane-5,7-dicarboxylate 151c, which was used in next step without purification. Crude yield: 100%. MS: calc'd (MH+) 362, measured (MH +) 362.

Workup

  1. additionAfter addition
  2. extractionextracted with DCM
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-a431fdb1c143438cba82868f27cedff9
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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