Methanol → HCID 68502098, compound

HRID 900502Notes

Reaction equation

HRID 900502 reaction equation
C[Si](C)(C)[N:3]1[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]([O:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1=[O:18].C(N(CC)CC)C.CO>>[CH3:15][Si:14]([CH3:17])([CH3:16])[O:13][C@H:5]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:3][C:4]1=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 11988558HCID 11988558, compound

Product 1

HCID 68502098HCID 68502098, compoundYield 87%

Conditions

Temperature
0 °C

Procedure

To a solution of N-trimethylsilyl-3-trimethylsiloxy-4-phenyl-azetidin-2-one (140 g, 0.46 mol) in hexanes (600 mL) at ambient temperature was added triethylamine (101 g, 1 mol), methanol (22 g, 0.7 mol) and the mixture was stirred for 15 minutes resulting in crystal formation of the N-desilylated product. The mixture was cooled to 0° C. for 15 min and the white crystals were collected by vacuum filtration, washed with cold hexanes, and dried to a constant weight of 94 g (87% yield). Mp: 118 to 120° C., 1H NMR (400 MHz, CDCl3) δ (ppm): −0.08 (s, 9H), 4.79 (d, J=4.4 Hz, 1H), 5.09 (dd, J=4.4, 2.7 Hz, 1H), 6.16 (bm, 1H), 7.3 to 7.4 (m, 5H).

Workup

  1. customresulting in crystal formation of the N-desilylated product
  2. filtrationthe white crystals were collected by vacuum filtration
  3. washwashed with cold hexanes
  4. customdried to a constant weight of 94 g (87% yield)

Sources & evidence

ORD record
ord-870debcb492448abb4196a5b9b2a2e8c
Source dataset
uspto-grants-2008_04
Patent number
US07358378B2

Reaction notes

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