Triethylamine → 4-Methoxybenzyl (RS)-2-hydroxy-2-[4-[(2RS,5SR)-5-methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio)-3-phenylacetamidoazetidin-2-on-1-yl]acetate

HRID 376605Notes

Reaction equation

HRID 376605 reaction equation
O.[C:2]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=[O:5])[CH:3]=[O:4].[CH3:16][O:17][C:18]([CH:20]1[O:24][CH:23]([C:25]([CH2:27][S:28][C@H:29]2[NH:32][C:31](=[O:33])[C@H:30]2[NH:34][C:35](=[O:43])[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:26])[CH2:22][CH2:21]1)=[O:19].C(N(CC)CC)C>ClC(Cl)C>[OH:4][CH:3]([N:32]1[CH:29]([S:28][CH2:27][C:25]([CH:23]2[CH2:22][CH2:21][CH:20]([C:18]([O:17][CH3:16])=[O:19])[O:24]2)=[O:26])[CH:30]([NH:34][C:35](=[O:43])[CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]1=[O:33])[C:2]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18780117HCID 18780117, compoundHCID 67907703(3R,4R)-4-[(2RS,5SR)-5-Methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio)-3-phenylacetamidoazetidin-2-one

Product 1

HCID 867551044-Methoxybenzyl (RS)-2-hydroxy-2-[4-[(2RS,5SR)-5-methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio)-3-phenylacetamidoazetidin-2-on-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

4-Methoxybenzyl glyoxylate hydrate (1.50g) in dichloroethane (30ml) was heated at reflux for 1h using a Dean and Stark apparatus for heavy entrainers. The mixture was cooled to room temperature and then a solution of (3R,4R)-4-[(2RS,5SR)-5-methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio]-3-phenylacetamidoazetidin-2-one (2.208g) in dichloroethane (20ml) was added followed by triethylamine (0.1ml). The mixture was stirred at room temperature for 1h and then the solvents were evaporated. The title compound was obtained as a mixture of isomers (2.66g) by column chromatography of the residue using gradient elution (silica gel, 1:1 hexane:ethyl acetate going to neat ethyl acetate); vmax (CHCl3) 3412, 1776, 1741 and 1681cm-1.

Workup

  1. customthe solvents were evaporated

Sources & evidence

ORD record
ord-62ac6919c7854f63b50569930f2b5273
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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