Methanol → HCID 118292740, compound

HRID 1486857Notes

Reaction equation

HRID 1486857 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH2:19][C:18]([CH2:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])([C:20](=O)[CH:21]=[N+]=[N-])[O:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C[OH:41].C1[CH2:46][O:45]CC1>C([O-])(=O)C1C=CC=CC=1.[Ag+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH2:19][C:18]([CH2:25][C:26]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27])([CH2:20][C:21]([O:45][CH3:46])=[O:41])[O:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 131736826HCID 131736826, compound

Product 1

HCID 118292740HCID 118292740, compound

Reagents, catalysts & solvents 1

HCID 164649Silver benzoateCatalyst

Procedure

Silver benzoate (0.393 g) was added to a mixture of butyl (3-(3-(benzyloxy)phenyl)-5-(diazoacetyl)-4,5-dihydro-1,2-oxazol-5-yl)acetate (1.87 g), triethylamine (1.496 mL), methanol (40 mL), and THF (20 mL) at 50 C, and the obtained mixture was stirred at 50 C for 20 minutes. The precipitate was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (0.919 g).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-012b723fcb794e70800f982635915883
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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