Ethyl orthoformate → HCID 178461475, compound

HRID 536696Notes

Reaction equation

[CH:1](OCC)(OCC)OCC.[NH:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]([N:22]3[CH2:29][CH2:28][C@:27]4([CH3:32])[C@H:30]([CH3:31])[C@H:23]3[CH2:24][C:25]3[CH:36]=[CH:35][C:34]([C:37]([NH:39][OH:40])=[NH:38])=[CH:33][C:26]=34)=[O:21])=[CH:19][C:14]=2[N:13]=[CH:12]1>>[NH:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]([N:22]3[CH2:29][CH2:28][C@:27]4([CH3:32])[C@H:30]([CH3:31])[C@H:23]3[CH2:24][C:25]3[CH:36]=[CH:35][C:34]([C:37]5[N:38]=[CH:1][O:40][N:39]=5)=[CH:33][C:26]=34)=[O:21])=[CH:19][C:14]=2[N:13]=[CH:12]1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 178461477HCID 178461477, compound

Product 1

HCID 178461475HCID 178461475, compound

Conditions

Temperature: 100 °C

Procedure

A mixture of triethyl orthoformate (4 mL) and (2R,6R,11S)-3-(1H-benzoimidazole-5-carbonyl)-N-hydroxy-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine-8-carboxamidine (0.25 g) is stirred at 100° C. for 6 h. After cooling to room temperature, the mixture is concentrated and the residue is purified by HPLC on reversed phase (water/MeCN/NH3) to give the title compound as a white solid.

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture is concentrated
customthe residue is purified by HPLC on reversed phase (water/MeCN/NH3)

Sources & evidence

ORD record: ord-d5485f987c8d47cca7d3bae98e5eee4f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859580B2

Reaction notes

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