Diazomethane → 2-(5-(((2s)-2-(1-Adamantylmethoxycarbonylamino)-2-tert-butoxycarbonyl-ethyl)carbamoyl)-2-thienyl)-cyclopropancarboxylic acid methyl ester

HRID 413216Notes

Reaction equation

HRID 413216 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH:4]=[CH:5][C:6]1[S:7][C:8]([C:11](=[O:37])[NH:12][CH2:13][C@H:14]([NH:22][C:23]([O:25][CH2:26][C:27]23[CH2:36][CH:31]4[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]4)[CH2:28]2)[CH2:34]3)=[O:24])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:10]=1.[N+](=[CH2:41])=[N-]>CCOCC.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:1][O:2][C:3]([CH:4]1[CH2:41][CH:5]1[C:6]1[S:7][C:8]([C:11](=[O:37])[NH:12][CH2:13][C@H:14]([NH:22][C:23]([O:25][CH2:26][C:27]23[CH2:36][CH:31]4[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]4)[CH2:28]2)[CH2:34]3)=[O:24])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:10]=1)=[O:38]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 571433013(5-(((2s)-2-(1-Adamantylmethoxycarbonylamino)-2-tert-butoxycarbonyl-ethyl)carbamoyl)-2-thienyl)-acrylic acid methyl ester

Product 1

HCID 572486992-(5-(((2s)-2-(1-Adamantylmethoxycarbonylamino)-2-tert-butoxycarbonyl-ethyl)carbamoyl)-2-thienyl)-cyclopropancarboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

The compound was synthesized analogously to example 3, step b) from 108 mg (0.2 mmol) of 3-(5-(((2S)-2-(1-adamantylmethoxycarbonylamino)-2-tert-butoxycarbonylethyl)carbamoyl)-2-thienyl)-acrylic acid methyl ester and a diazomethane solution in ether (generated from 0.5 g of N-nitroso-N-methyl-urea) in the presence of 10 mg palladium diacetate. 105 mg of a colourless oil were obtained which was sufficiently pure for use in the subsequent step.

Sources & evidence

ORD record
ord-acac8004e8fd4a94a9e4e50331f72b5f
Source dataset
uspto-grants-2003_05
Patent number
US06566366B1

Reaction notes

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