4-Methylmorpholine → HCID 67092728, compound

HRID 1261848Notes

Reaction equation

HRID 1261848 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:16]([CH3:17])[C:15](=[O:18])[N:14]2[C@@H:19]([CH2:22][C:23]([OH:25])=O)[CH2:20][O:21][CH:13]2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:27]1[C:29]2([CH2:34][CH2:33][NH:32][CH2:31][C@H:30]2[OH:35])[CH2:28]1.CN1CCOCC1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[C@@H:16]([CH3:17])[C:15](=[O:18])[N:14]2[C@@H:19]([CH2:22][C:23]([N:32]3[CH2:33][CH2:34][C:29]4([CH2:27][CH2:28]4)[C@H:30]([OH:35])[CH2:31]3)=[O:25])[CH2:20][O:21][CH:13]2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochlorideHCID 67092976HCID 67092976, compound

Product 1

HCID 67092728HCID 67092728, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (138 mg, 0.36 mmol) was added to a solution of (3S,6S)-3-carboxymethyl-6-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyrazine-7-carboxylic acid benzyl ester (84 mg, 0.24 mmol), (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (39 mg, 0.24 mmol) and 4-methylmorpholine (73 mg, 0.73 mmol) in DMF(1 mL), then after 16 h the reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; DCM→DCM/MeOH/25% aq. ammonia solution 90:10:0.25) afforded the title compound (106 mg, 96%). Colourless gum, MS: 458.5 (M+H)+.

Workup

  1. customafter 16 h the reaction mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-41ddbb79d0a94158ad5b43f3eb6fba7e
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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