Sodium borohydride → HCID 66843270, compound

HRID 254054Notes

Reaction equation

HRID 254054 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@@H:10]([NH:14][C:15](=[O:51])[CH2:16][NH:17][C:18](=[O:50])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C@@H:27]3[C@@H:30]([S:31][CH2:32][C:33]([C:35]4[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=4)=[O:34])[C:29](=[O:42])[N:28]3[C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)=[CH:23][CH:22]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CO.C(O)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@@H:10]([NH:14][C:15](=[O:51])[CH2:16][NH:17][C:18](=[O:50])[CH2:19][O:20][C:21]2[CH:22]=[CH:23][C:24]([C@@H:27]3[C@@H:30]([S:31][CH2:32][CH:33]([C:35]4[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=4)[OH:34])[C:29](=[O:42])[N:28]3[C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)=[CH:25][CH:26]=2)[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66842984HCID 66842984, compound

Product 1

HCID 66843270HCID 66843270, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

(2R)-3-(4-cyanophenyl)-2-{[({[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}amino}acetyl]amino)propanoic acid (0.006 g, 0.0084 mmole) was dissolved in methanol (1.5 ml). NaBH4 (0.0035 g, 0.092 mmole) was added and when the reaction was complete according to LC-MS a few drops of acetic acid was added. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC on a Kromasil C8-column using a stepwise gradient of 33.5%, 43% and then 55.5% MeCN in 0.1M ammonium acetate buffer as eluent. After freeze-drying, 0.005 g (83%) of the desired product was obtained.

Workup

  1. additionwas 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-c3019296f6b749bf97ee1272159a5c63
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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