Sodium borohydride → HCID 68426741, compound

HRID 254021Notes

Reaction equation

HRID 254021 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:46]=[CH:45][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:33][C:34]([NH:36][C@H:37]([C:42]([OH:44])=[O:43])[CH2:38][C:39](=[O:41])[NH2:40])=[O:35])=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[OH:16])[C@H:9]2[C:24]2[CH:46]=[CH:45][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:33][C:34]([NH:36][C@H:37]([C:42]([OH:44])=[O:43])[CH2:38][C:39](=[O:41])[NH2:40])=[O:35])=[O:31])=[CH:26][CH:25]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66842730HCID 66842730, compound

Product 1

HCID 68426741HCID 68426741, compoundYield 80%

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-L-asparagine (0.020 g, 0.031 mmol) was dissolved in methanol (2 ml). NaBH4 (0.004 g, 0.106 mmol) was added and when 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 35% MeCN in 0.1M ammonium acetate buffer as eluent. After freeze-drying, 0.016 g (80%) of the title product was obtained. NMR (400 MHz, CD3COOD) 2.62 (dd 1H), 2.73 (dd, 1H), 2.90-3.07 (m, 2H), 3.89-4.08 (m, 3H), 4.55 (dd, 1H), 4.60 (ABq, 2H), 4.78-4.85 (m, 1H), 4.90 (d, 0.5H), 4.92 (d, 0.5H), 6.96-7.09 (m, 6H), 7.24-7.38 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-3a36ecce1814480a90f52e9afe802a46
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

Loading…