Water → HCID 54478606, compound

HRID 1789889Notes

Reaction equation

HRID 1789889 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([CH2:23][SH:24])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:11]([CH2:13][OH:14])[CH:12]=1)[CH3:2].[NH4+].[Cl-].O.[C:29](OC(=O)C)(=[O:31])[CH3:30]>>[CH2:1]([O:3][C:4](=[O:25])[CH:5]([CH2:23][S:24][C:29](=[O:31])[CH3:30])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])=[C:11]([CH2:13][OH:14])[CH:12]=1)[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 54423256HCID 54423256, compound

Product 1

HCID 54478606HCID 54478606, compoundYield 60%

Procedure

A mixture of crude 3-(6-tert-butoxycarbonylamino-5-hydroxymethyl-pyridin-3-yl)-mercaptomethyl-propionic acid ethyl ester (0.38 g, 1.0 mmol) and KHCO3 (0.11 g, 1.1 mmol) in acetic acid anhydride (1 mL) was stirred at room temperature for 5 h. NH4Cl (sat.) and water was then added. The mixture was extracted with dichloromethane, dried and concentrated under reduced pressure. Flash chromatography (CH2Cl2, 2.5% MeOH in CH2Cl2) gave 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-5-hydroxymethyl-pyridin-3-yl)-propionic acid ethyl ester (0.23 g, 60%).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d7aa3ea792444ddbc0e9d6402f114d6
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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