Methanol → HCID 58904484, compound

HRID 1292746Notes

Reaction equation

HRID 1292746 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C@@H:10]([C@@:14]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[NH:20][CH2:19][C:18](=[O:21])[N:17]([CH3:22])[C:16]3[CH:23]=[CH:24][CH:25]=[CH:26][C:15]2=3)[C:11]([OH:13])=[O:12])[N:3]=1.[CH3:33]O>O.C=O.[Pd]>[CH3:22][N:17]1[C:16]2[CH:23]=[CH:24][CH:25]=[CH:26][C:15]=2[C@:14]([C@H:10]([O:9][C:4]2[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=2)[C:11]([OH:13])=[O:12])([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:20]([CH3:33])[CH2:19][C:18]1=[O:21]

Participants

6

Reactant 2

HCID 887MethanolHCID 10224745HCID 10224745, compound

Product 1

HCID 58904484HCID 58904484, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 712FormaldehydeSolventHCID 962WaterSolvent

Procedure

Pd/C (100 mg, 10% Pd) is added to a solution of (±)-(S*)-(4,6-dimethyl-pyrimidin-2-yloxy)-((5S*)-1-methyl-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl)-acetic acid (100 mg, 0.231 mmol, Example 49) in water (8 ml), methanol (8 ml) and aq. formaldehyde solution (0.2 ml, 36%). The mixture is stirred at rt under 3 atm H2 for 18 h before the catalyst is filtered off. The organic solvent of the filtrate is evaporated and the remaining aq. phase is extracted three times with DCM. The organic phase is evaporated and the product is purified by chromatography on prep. tlc-plattes with DCM:methanol 9:1 to give (±)-(S*)-((5S*)-1,4-dimethyl-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl)-(4,6-dimethyl-pyrimidin-2-yloxy)-acetic acid (57 mg) as a white powder. LC-MS2: tR=3.40 min, [M+1]+=447.10, [M−1]−=445.14.

Workup

  1. filtrationis filtered off
  2. customThe organic solvent of the filtrate is evaporated
  3. extractionthe remaining aq. phase is extracted three times with DCM
  4. customThe organic phase is evaporated
  5. customthe product is purified by chromatography on prep

Sources & evidence

ORD record
ord-246b4b49e7514e2cb313bac7f3b1dcaa
Source dataset
uspto-grants-2007_07
Patent number
US07238685B2

Reaction notes

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