Diethylamine → (3R,4S,5S)-tert-butyl 4-((S)-2-amino-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate
Reaction equation
C1C2C(COC([NH:18][C@H:19]([C:23]([N:25]([CH3:42])[C@@H:26]([C@@H:38]([CH3:41])[CH2:39][CH3:40])[C@H:27]([O:36][CH3:37])[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:24])[CH:20]([CH3:22])[CH3:21])=O)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C>O1CCCC1.CC1CCCO1>[CH3:37][O:36][C@@H:27]([C@@H:26]([N:25]([CH3:42])[C:23](=[O:24])[C@H:19]([CH:20]([CH3:22])[CH3:21])[NH2:18])[C@@H:38]([CH3:41])[CH2:39][CH3:40])[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of #5 (26 g, 42 mmol, 1 eq.) in tetrahydrofuran (260 mL, 0.16 M) was added diethylamine (22 mL) over 30 minutes. The reaction was stirred for about 6 hours and the suspension was then filtered through Celite and washed with additional tetrahydrofuran (25 mL). The filtrate was concentrated in vacuo to provide a pale yellow oil, which was redissolved in 2-methyltetrahydrofuran (50 mL) and concentrated again to ensure complete removal of diethylamine. The crude oil of #6 (>15.25 g) was taken into the next step without further purification.
Workup
- filtrationthe suspension was then filtered through Celite
- washwashed with additional tetrahydrofuran (25 mL)
- concentrationThe filtrate was concentrated in vacuo
- customto provide a pale yellow oil, which
- concentrationconcentrated again
- customremoval of diethylamine
- customThe crude oil of #6 (>15.25 g) was taken into the next step without further purification
Sources & evidence
- ORD record
- ord-330256b9f614413282285c495cc8f27d
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09138486B2
Reaction notes
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