Triethylamine → 1,1-Dimethylethyl (9S)-9-[[(phenylmethoxy)carbonyl]amino]-1-oxa-7-azaspiro[4.4]nonane-7-carboxylate

HRID 1025688Notes

Reaction equation

HRID 1025688 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][C:13]1([OH:28])[CH2:24][CH2:25][CH2:26]O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:13]2([O:28][CH2:26][CH2:25][CH2:24]2)[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59556045HCID 59556045, compound

Product 1

HCID 595560551,1-Dimethylethyl (9S)-9-[[(phenylmethoxy)carbonyl]amino]-1-oxa-7-azaspiro[4.4]nonane-7-carboxylateYield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.80 g of the diol of step D in 15 mL of dichloromethane at 0° C. were added 0.2 mL of methanesulfonyl chloride and 0.8 mL of triethylamine. After being stirred for 1 hour, the mixture was refluxed at 60° C. overnight. Solvent was removed under vacuum. The residue was taken up in EtOAc/water and the two phases were separated. The water phase was extracted with EtOAc twice. The combined organic was dried over Na2SO4. Solvent was removed under vacuum. Column chromatography on silica gel using 15% EtOAc/hexane to 100% EtOAc as eluent provided 0.32 g of the title compound. MS (M+H)+ 377.

Workup

  1. customSolvent was removed under vacuum
  2. customthe two phases were separated
  3. extractionThe water phase was extracted with EtOAc twice
  4. dry with materialThe combined organic was dried over Na2SO4
  5. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-4546351528b64b0ab05838dc8e5ca8bc
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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