Sodium borohydride → HCID 16039301, compound

HRID 2252454Notes

Reaction equation

HRID 2252454 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:47])[CH2:9][CH2:10][C@H:11]2[C:14](=[O:15])[N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]2[C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C@H:34]([OH:45])[C@H:35]4[O:41][CH:39]([OH:40])[C@H:38]([OH:42])[C@@H:37]([OH:43])[C@@H:36]4[OH:44])[CH:29]=3)=[CH:24][C:23]=2[OH:46])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(#N)C.O.C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([OH:47])[CH2:9][CH2:10][C@H:11]2[C:14](=[O:15])[N:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C@@H:12]2[C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C@H:34]([OH:45])[C@@H:35]([OH:41])[C@@H:36]([OH:44])[C@H:37]([OH:43])[C@@H:38]([OH:42])[CH2:39][OH:40])[CH:29]=3)=[CH:24][C:23]=2[OH:46])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 16039300HCID 16039300, compound

Product 1

HCID 16039301HCID 16039301, compoundYield 22%

Reagents, catalysts & solvents 2

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

Procedure

(6S)-6-C-(4′-{(2S,3R)-3-[(3S)-3-(4-Fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}-3′-hydroxybiphenyl-3-yl)-D-glucopyranose (7.1 mg, 0.01 mmol) was dissolved in 80:20 acetonitrile-water (1 mL). Sodium borohydride (0.4 mg, 0.01 mmol) was added at room temperature and the reaction was stirred for 30 min monitoring by LCMS. Upon completion, the reaction was diluted with 80:20 acetonitrile:water (3 mL) then filtered through a Whatman 0.45 μM glass microfiber filter 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 (6S)-6-C-(4′-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}-3′-hydroxybiphenyl-3-yl)-D-glucitol (1.4 mg, 22% yield). 1H NMR (300 MHz, CDCl3/CD3OD) δ 7.37-6.89 (m, 16H), 5.08 (d, J=2.4 Hz, 1H), 4.97-4.95 (m, 1H), 4.60 (t, J=6.0 Hz, 1H), 3.92 (m, 1H), 3.76-3.56 (m, 6H), 2.01-1.82 (m, 4H) ppm; MS [M−OH]+ 629.8.

Workup

  1. filtrationwater (3 mL) then filtered through a Whatman 0.45 μM glass microfiber
  2. filtrationfilter
  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-e5e07ff2d5c54e21bbbd8522038331f7
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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