Water → HCID 16093498, compound

HRID 2252452Notes

Reaction equation

HRID 2252452 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[CH:25]=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([C@@H:36]3[C@@H:39]([CH2:40][CH2:41][C@@H:42]([C:44]4[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=4)[OH:43])[C:38](=[O:51])[N:37]3[C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[CH:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1)(=O)C.C(N(CC)CC)C.O>CO>[F:50][C:47]1[CH:48]=[CH:49][C:44]([C@@H:42]([OH:43])[CH2:41][CH2:40][C@H:39]2[C:38](=[O:51])[N:37]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[C@@H:36]2[C:33]2[CH:32]=[CH:31][C:30]([C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([C@@H:6]4[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]4[OH:4])[CH:25]=3)=[CH:35][CH:34]=2)=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 69257981HCID 69257981, compound

Product 1

HCID 16093498HCID 16093498, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S)-2,3,4,6-Tetra-O-acetyl-1,5-anhydro-1-(4′-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl)-D-glucitol (10.5 mg, 0.013 mmol) was dissolved in 0.30 mL of methanol and 0.30 mL of triethylamine followed by drop-wise addition of water (0.80 mL). The yellowish mixture stirred at room temperature overnight. LCMS of the solution confirmed complete consumption of the starting material and formation of the fully deprotected material. The mixture was concentrated in vacuo, and purified by reverse-phase HPLC (Polaris C18-A 10 μ 250×21.2 mm column, 30% to 95% acetonitrile-0.1% trifluoroacetic acid in water) to afford 2.8 mg (35%) of the desired (1S)-1,5-anhydro-1-(4′-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl)-D-glucitol as a white powder; 1H NMR (300 MHz, CD3OD) δ 7.65 (d, J=11.1 Hz, 2H), 7.54-7.23 (m, 10H), 7.05-6.89 (m, 3H), 4.61 (t, J=6.3 Hz, 1H), 4.19 (d, J=9.0 Hz, 1H), 3.87 (d, J=10.7 Hz, 1H), 3.73-3.63 (m, 1H), 3.49-3.36 (m, 3H) 3.22-3.18 (m, 2H), 1.89 (m, 4H) ppm; MS [M−OH]+ 596.5.

Workup

  1. customconsumption of the starting material and formation of the fully deprotected material
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by reverse-phase HPLC (Polaris C18-A 10 μ 250×21.2 mm column, 30% to 95% acetonitrile-0.1% trifluoroacetic acid in water)

Sources & evidence

ORD record
ord-82071934372b41b3a666eba653a83588
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

Loading…