Methanol, magnesium salt (2:1) → HCID 66986838, compound

HRID 2109503Notes

Reaction equation

HRID 2109503 reaction equation
C([N:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@H:10]([CH2:15][N:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]([O:13][CH3:14])=[O:12])(=O)C1C=CC=CC=1.C[O-].[Mg+2].C[O-]>CO>[C:32]([O:31][C:29]([NH:9][C@@H:10]([CH2:15][N:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 164537Methanol, magnesium salt (2:1)HCID 66986662HCID 66986662, compound

Product 1

HCID 66986838HCID 66986838, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.3 g of methyl (S)-2-(benzoyl-tert-butoxycarbonylamino)-3-diphenylaminopropionate were dissolved in 13 ml of methanol and admixed with 2.74 ml of a 1M solution of magnesium methoxide in methanol. The solution was stirred at RT overnight and concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed with water. The ethyl acetate phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was crystallized from a little diisopropyl ether/heptane. Yield: 0.95 g (90% of theory) 1H NMR: 1.38 (s, 9H), 3.55 (s, 3H), 4.10-4.25 (m, 2H), 4.50-4.62 (m, 1H), 5.10-5.25 (m, 1H), 6.90-7.05 (m, 6H), 7.20-7.30 (m, 4H)

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with water
  3. dry with materialThe ethyl acetate phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from a little diisopropyl ether/heptane

Sources & evidence

ORD record
ord-764f24e964584a5cb50c835230736b16
Source dataset
uspto-grants-2009_04
Patent number
US07514578B2

Reaction notes

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