Diethyl Ether → HCID 69838250, compound

HRID 352709Notes

Reaction equation

[C:1]([O:5][C:6](=[O:32])[C:7](=N)[CH2:8][C@H:9]([NH:13][C:14]([O:16][CH2:17][CH:18]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])C(Cl)O)([CH3:4])([CH3:3])[CH3:2].[C:33]([O:38][CH3:39])(=[O:37])[C:34]([CH3:36])=[CH2:35].C([N:42]([CH:46](C)C)C(C)C)C.CC[O:51]CC>>[CH3:39][O:38][C:33]([C:34]1([CH3:36])[O:51][N:42]=[C:46]([C@@H:9]([NH:13][C:14]([O:16][CH2:17][CH:18]2[C:30]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:20]3[C:19]2=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])[CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:32])[CH2:35]1)=[O:37]

Participants

Reactant 4

HCID 3283Diethyl Ether

HCID 6658Methyl Methacrylate

HCID 81531Diisopropylethylamine

HCID 131724460HCID 131724460, compound

Product 1

HCID 69838250HCID 69838250, compound

Procedure

A solution of 4-(9-fluorenylmethoxycarbonyl)amino-(4S)-5-chloro-5-hydroxy-imino-pentanoic acid t-butyl ester (3.44 g, 7.50 mmol) and methyl methacrylate (2.40 mL, 3.0 eq) in dry ether under N2 at −78° C. was treated with EtN(i-Pr)2 (1.96 mL, 1.5 eq). Similar treatment as described previously followed by flash chromatography with 25-30% ethyl acetate/hexanes gave 3.46 g (89% overall) of the title compound as diastereomeric mixture.

Sources & evidence

ORD record: ord-23f679c12a4d4f1b950fc444ec44d6d0
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747050B1

Reaction notes

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