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

HRID 1421827Notes

Reaction equation

HRID 1421827 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 (1.50 g) in dichloroethane (30 ml) was heated at reflux for 1 h 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 (2.208 g) in dichloroethane (20 ml) was added followed by triethylamine (0.1 ml). The mixture was stirred at room temperature for 1 h and then the solvents were evaporated. The title compound was obtained as a mixture of isomers (2.66 g) by column chromatography of the residue using gradient elution (silica gel, 1:1 hexane:ethyl acetate going to neat ethyl acetate); νmax (CHCl3) 3412, 1776, 1741 and 1681 cm-1.

Workup

  1. temperatureat reflux for 1 h
  2. customthe solvents were evaporated

Sources & evidence

ORD record
ord-f1c163dbddd644279b3b0fba063c586a
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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