Water → HCID 131721504, compound

HRID 1421810Notes

Reaction equation

HRID 1421810 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)(=[O:4])[CH:2]=[O:3].O.[CH3:16][O:17][CH2:18][CH:19]1[O:23][CH:22]([C:24]([CH2:26][S:27][C@H:28]2[NH:31][C:30](=[O:32])[C@H:29]2[NH:33][C:34](=[O:43])[CH2:35][O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:25])[CH2:21][CH2:20]1.C(N(CC)CC)C>ClC(Cl)C.C(Cl)(Cl)Cl>[OH:3][CH:2]([N:31]1[C@H:28]([S:27][CH2:26][C:24]([CH:22]2[CH2:21][CH2:20][CH:19]([CH2:18][O:17][CH3:16])[O:23]2)=[O:25])[C@H:29]([NH:33][C:34](=[O:43])[CH2:35][O:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:30]1=[O:32])[C:1]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10867196Acetic acid, oxo-, (4-methoxyphenyl)methyl esterHCID 70256441HCID 70256441, compound

Product 1

HCID 131721504HCID 131721504, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

A solution of 4-methoxybenzyl glyoxylate (1.82 g) in dichloroethane (30 ml) was heated at reflux using a Dean and Stark water separator for 1 h. The solution was then cooled to room temperature and then (3R,4R)-4-[(2RS,5SR)-5-methoxymethyltetrahydrofuran-2-ylcarbonylmethylthio]-3-phenoxyacetamidoazetidin-2-one (2.94 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 removed on a rotary evaporator. The product was isolated as a mixture of isomers (3.23 g) by column chromatography of the residue (silica gel, ethyl acetate as eluent); νmax (CHCl3) 3411, 1780, 1745 and 1691 cm-1.

Workup

  1. temperatureat reflux
  2. customthe solvents were removed on a rotary evaporator
  3. customThe product was isolated as a mixture of isomers (3.23 g) by column chromatography of the residue (silica gel, ethyl acetate as eluent)

Sources & evidence

ORD record
ord-163a233beb9440ff80aec83a2614531e
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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