Hydrochloric Acid → HCID 10386495, compound

HRID 750935Notes

Reaction equation

HRID 750935 reaction equation
[BH4-].[Na+].[C:3]([C:5](=[C:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]3=[O:33])=[CH:19][C:18]=2[F:34])[CH2:13][CH2:12]1)[C:6](OCC)=[O:7])#[N:4].Cl>CO>[C:3]([CH:5]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][C@H:26]([CH2:28][NH:29][C:30](=[O:32])[CH3:31])[O:25][C:24]3=[O:33])=[CH:19][C:18]=2[F:34])[CH2:13][CH2:12]1)[CH2:6][OH:7])#[N:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10388730HCID 10388730, compound

Product 1

HCID 10386495HCID 10386495, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of sodium borohydride (5.26 mmol), (S)-N-{3-[4-(4-(1-cyano-1-ethoxycarbonyl-methylidene)-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (0.34 mmol) in methanol (15 ml) was stirred for 0.5 hours at room temperature. The reaction mixture was neutralized with dilute hydrochloric acid. The solid was filtered and purified on silica gel column chromatography recrystallized from chloroform:methanol to provide tile compound in 76% yield.

Workup

  1. filtrationThe solid was filtered
  2. custompurified on silica gel column chromatography
  3. customrecrystallized from chloroform
  4. custommethanol to provide tile compound in 76% yield

Sources & evidence

ORD record
ord-1f607e08897e4621834c4c793e670f9e
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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