Triethylamine → HCID 86608207, compound

HRID 405901Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:24])[N:10]([CH2:21][CH2:22][OH:23])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[CH:17]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl>[CH2:1]([O:8][C:9]([N:10]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[CH:17]2)[CH2:21][CH2:22][O:23][S:33]([CH3:32])(=[O:35])=[O:34])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2-hydroxy-ethyl)-(1H-indol-7-ylmethyl)-carbamic acid benzyl ester (2.79 g, 8.61 mmol) in dichloromethane (50 mL) was added triethylamine (1.56 mL, 11.2 mmol). The mixture was cooled to 0° C. and methanesulfonyl chloride (0.74 mL, 9.47 mmol) added in a dropwise manner. The mixture was warmed to room temperature and allowed to stir for 2 hours. The mixture was then quenched with water (30 mL) and 1.0 M sodium hydroxide (10 mL). The organic layer was separated and the aqueous layer extracted with dichloromethane (20 mL). The combined extracts were washed with 1.0 M hydrochloric acid (20 mL), water (30 mL), dried over anhydrous sodium sulfate and evaporated to dryness. Methanesulfonic acid 2-[benzyloxycarbonyl-(1H-indol-7-ylmethyl)-amino]-ethyl ester (3.46 g) was obtained as an oil

Workup

temperatureThe mixture was warmed to room temperature
customThe mixture was then quenched with water (30 mL) and 1.0 M sodium hydroxide (10 mL)
customThe organic layer was separated
extractionthe aqueous layer extracted with dichloromethane (20 mL)
washThe combined extracts were washed with 1.0 M hydrochloric acid (20 mL), water (30 mL)
dry with materialdried over anhydrous sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-1a65e95f69fb4f8b88a85d7bb3224522
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754078B2

Reaction notes

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