Isopropanol hydrochloride → cis-(+/-)-Tetrahydro-4-mercapto-2-furanmethanol 2-carbamate

HRID 1290351Notes

Reaction equation

HRID 1290351 reaction equation
[NH2:1][C:2]([O:4][CH2:5][C@H:6]1[O:10][CH2:9][C@@H:8]([S:11]C(=O)C)[CH2:7]1)=[O:3].C[O-].[Na+].CO.Cl.C(O)(C)C>O1CCCC1>[C:2]([O:4][CH2:5][C@H:6]1[CH2:7][C@@H:8]([SH:11])[CH2:9][O:10]1)(=[O:3])[NH2:1]

Participants

5

Reactant 3

HCID 21912024Isopropanol hydrochlorideHCID 23694274Sodium methanolate methanolHCID 86750313Ethanethioic acid cis-(+/-)-S-[5-[[(aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]ester

Product 1

HCID 131720645cis-(+/-)-Tetrahydro-4-mercapto-2-furanmethanol 2-carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under anhydrous conditions, 0.109 g of product from Example 10 dissolved in 1.75 ml of tetrahydrofuran, cooled in an ice bath, is treated, via syringe, with 120 microliter of sodium methoxide/methanol (25 wt % in methanol). The progress of the reaction is monitored by thin layer chromatography. After 20 minutes, 280 microliter of 1.86N hydrochloric acid/isopropyl alcohol is added and the reaction is stirred for 5 minutes. The reaction is concentrated in vacuo to give the desired product as a white solid which is used as is in the following reaction.

Workup

  1. temperaturecooled in an ice bath
  2. concentrationThe reaction is concentrated in vacuo

Sources & evidence

ORD record
ord-69f2c3c398314cec8825866dd492a3f6
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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