Methanol → HCID 89515508, compound

HRID 1778569Notes

Reaction equation

HRID 1778569 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:31])[C:9]([CH2:28][CH:29]=O)([CH2:15][CH2:16][CH2:17][CH2:18][B:19]1[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][NH:33]1.CO>ClCCl>[C:1]([O:5][C:6]([N:8]([CH3:31])[C:9]([CH2:28][CH2:29][N:33]1[CH2:34][C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:32]1)([CH2:15][CH2:16][CH2:17][CH2:18][B:19]1[O:20][C:21]([CH3:27])([CH3:26])[C:22]([CH3:24])([CH3:25])[O:23]1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 422478IsoindolineHCID 89514332HCID 89514332, compound

Product 1

HCID 89515508HCID 89515508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(tert-butoxycarbonyl(methyl)amino)-2-(2-(isoindolin-2-yl)ethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate was prepared in accordance with the procedure of step 6 in Example 27 except that ethyl 2-(tert-butoxycarbonyl(methyl)amino)-2-(2-oxoethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate was used instead of 3-phenylpropanal and isoindoline was used instead of (R)-2-acetamido-2-((1s,3S)-3-aminocyclobutyl)-N-tert-butyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide hydrochloride. Rf 0.32 (10% MeOH in dichloromethane). 1H NMR (CDCl3, 300 MHz) δ 7.20-7.14 (m, 4H), 4.13 (q, J=8.0 Hz, 2H), 3.96 (br s, 4H), 3.00-2.88 (m, 4H), 2.75-2.60 (m, 2H), 2.41-2.31 (m, 1H), 2.15-1.95 (m, 2H), 1.87-1.74 (m, 2H), 1.49-1.08 (m, 26H), 0.79 (t, J=8.5 Hz, 2H). ESI MS found for C30H49B1N2O6 m/z [545.6 (M+1)].

Sources & evidence

ORD record
ord-bb909735f1794a57887bf6c68ade3b8b
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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