Triethylamine → Methanesulfonic acid 2-(4-{[4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-3-methanesulfonyloxy-propyl ester

HRID 1508143Notes

Reaction equation

[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]([CH2:16][OH:17])[CH2:14][OH:15])[CH:10]=[CH:9][C:8]=2[NH:18][C:19]([C:21]2[N:22]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:23]=[C:24]([C:26]#[N:27])[N:25]=2)=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CCN(CC)CC.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C(Cl)Cl>[C:26]([C:24]1[N:25]=[C:21]([C:19]([NH:18][C:8]2[CH:9]=[CH:10][C:11]([CH:13]([CH2:14][O:15][S:44]([CH3:43])(=[O:46])=[O:45])[CH2:16][O:17][S:44]([CH3:43])(=[O:46])=[O:45])=[CH:12][C:7]=2[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=2)=[O:20])[N:22]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:34])([CH3:33])[CH3:35])[CH:23]=1)#[N:27]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-hydroxy-1-hydroxymethyl-ethyl)-phenyl]-amide (0.600 g, 1.21 mmol, as prepared in the previous step) in CH2Cl2 (25 mL) was cooled to 0° C. and was treated with Et3N (421 μL, 3.02 mmol) and methanesulfonyl chloride (190 μL, 2.42 mmol). The mixture was stirred at 0° C. for 2 h, diluted with CH2Cl2, and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo. Silica gel chromatography of the residue with 25-50% EtOAc-hexane afforded the title compound (0.551 g, 70%) as a white solid. Mass spectrum (APCI, m/z): Calcd. for C28H40N4O8S2Si, 653.2 (M+H). found 652.8.

Workup

washwashed with water
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-149bbdfe310c4e90bcec4ab12eb48796
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221797B2

Reaction notes

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