Sodium borohydride → HCID 11181315, compound

HRID 2252458Notes

Reaction equation

HRID 2252458 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:13](=[O:14])[C@H:12]([CH2:15][CH2:16][C@@H:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[OH:18])[C@H:11]2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH2:39][C@H:40]4[O:46][CH:44]([OH:45])[C@H:43]([OH:47])[C@@H:42]([OH:48])[C@@H:41]4[OH:49])[CH:33]=3)=[CH:28][CH:27]=2)=[CH:6][CH:5]=1>C(#N)C.O.C(#N)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:13](=[O:14])[C@H:12]([CH2:15][CH2:16][C@@H:17]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[OH:18])[C@H:11]2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH2:39][C@@H:40]([OH:46])[C@@H:41]([OH:49])[C@H:42]([OH:48])[C@@H:43]([OH:47])[CH2:44][OH:45])[CH:33]=3)=[CH:28][CH:27]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11239169HCID 11239169, compound

Product 1

HCID 11181315HCID 11181315, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Sodium borohydride (1.6 mg, 0.04 mmol) was added to 6-O-(4′-{(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}biphenyl-3-yl)-D-glucopyranose (26.3 mg, 0.04 mmol) dissolved in 80:20 acetonitrile-water (1 mL) at room temperature. The reaction was stirred for 10 min at room temperature monitoring by LCMS. Upon completion, the reaction was diluted with 50:50 acetonitrile:water (3 mL) and filtered through a Whatman 0.45 μM glass microfiber filter then purified by preparative HPLC (Polaris C18-A 10 μ 250×21.2 mm column, 30% to 95% acetonitrile-0.1% trifluoroacetic acid in water) affording 6-O-(4′-{(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}biphenyl-3-yl)-D-glucitol (21.2 mg, 80% yield). 1H NMR (300 MHz, CDCl3/1% CD3OD) δ 7.58 (d, J=8.1 Hz, 2H), 7.39-7.24 (m, 7H), 7.17-7.15 (m, 2H), 7.04-6.92 (m, 5H), 4.71 (d, J=2.1 Hz, 1H), 4.68 (t, J=6.3 Hz, 1H), 4.31-4.27 (m, 1H), 0.19-4.14 (m, 1H), 4.08-4.02 (m, 1H), 3.97-3.95 (m, 1H), 3.86-3.65 (m, 4H), 3.14-3.12 (m, 1H), 2.01-1.88 (m, 4H) ppm; MS [M+HCO2−]− 694.0.

Workup

  1. filtrationwater (3 mL) and filtered through a Whatman 0.45 μM glass microfiber
  2. filtrationfilter
  3. customthen purified by preparative 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-4b653cb12a7e4cd696a298a78aa61e84
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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