Sodium borohydride → HCID 68425894, compound

HRID 254065Notes

Reaction equation

HRID 254065 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:24]2[CH:49]=[CH:48][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:33][C:34]([NH:36][C@H:37]([C:45]([OH:47])=[O:46])[CH2:38][CH2:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])=[O:35])=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(O)(=O)C>[C:45]([OH:47])(=[O:46])[CH3:37].[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[OH:16])[C@H:9]2[C:24]2[CH:49]=[CH:48][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:33][C:34]([NH:36][C@H:37]([C:45]([OH:47])=[O:46])[CH2:38][CH2:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])=[O:35])=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68425005HCID 68425005, compound

Product 1

HCID 68425894HCID 68425894, compoundYield 150.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycyl-N6,N6-dimethyl-L-lysine (0.05 g, 0.007 mmole) was dissolved in methanol (1.5 mL). NaBH4 (0.0065 g, 0.0172 mmole) was added and after about 15 min the reaction was complete according to LC-MS. A few drops of acetic acid were added. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC on a Kromasil C8-column using 33.5% MeCN in 0.1M ammonium acetate buffer as eluent. After freeze-drying, 0.004 g (73%) of the desired product as the acetate-salt was obtained.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative HPLC on a Kromasil C8-column
  3. customAfter freeze-drying

Sources & evidence

ORD record
ord-051f7bdba963496db8cee34067b177df
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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