Isopropanol hydrochloride → trans-(+/-)-N-[(Tetrahydro-4-mercapto-2-furanyl)methyl]-N-(phenylmethoxy)acetamide

HRID 54780Notes

Reaction equation

HRID 54780 reaction equation
[C:1]([N:4]([CH2:13][C@@H:14]1[O:18][CH2:17][C@@H:16]([S:19]C(=O)C)[CH2:15]1)[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].C[O-].[Na+].CO.Cl.C(O)(C)C>O1CCCC1>[SH:19][C@@H:16]1[CH2:17][O:18][C@@H:14]([CH2:13][N:4]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:1](=[O:3])[CH3:2])[CH2:15]1

Participants

5

Reactant 3

HCID 21912024Isopropanol hydrochlorideHCID 23694274Sodium methanolate methanolHCID 86750754Ethanethioic acid trans-(+/-)-S-[5-[[Acetyl(phenylmethoxy)amino]methyl]tetrahydro-3-furanyl]ester

Product 1

HCID 86750753trans-(+/-)-N-[(Tetrahydro-4-mercapto-2-furanyl)methyl]-N-(phenylmethoxy)acetamideYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared by the procedure of Example 16 using 0.390 g of product from Example 72, 0.580 ml of 25% sodium methoxide/methyl alcohol, 0.850 ml of tetrahydrofuran and 1.26 ml of 2N hydrochloric acid/isopropyl alcohol to give 0.205 g of the desired product.

Sources & evidence

ORD record
ord-90eaad4618504011afff5937789a029e
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

Loading…