Hydrochloric Acid → HCID 66674585, compound

HRID 505395Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH3:41])[CH2:9][CH2:10][N:11]([CH3:40])[C:12](=[O:39])[CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25]C)=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1.O.CO>[C:1]([O:5][C:6]([N:8]([CH3:41])[CH2:9][CH2:10][N:11]([CH3:40])[C:12](=[O:39])[CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([OH:25])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

The crude methyl 1-{2-[{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}(methyl)amino]-2-oxoethyl}-3-cyclohexyl-2-phenyl-1H-indole-6-carboxylate in dioxane/H2O/MeOH solution (1:1:1; 0.06 M) was treated with an aqueous solution of KOH (5N) (3 eq). The solution was stirred at 60° C. for 4 h. The volume of the solution was reduced in vacuo, and the mixture acidified with HCl (1N) before extracting with EtOAc (2×). The combined organic fractions were washed with brine, before being dried over Na2SO4, filtered and concentrated in vacuo. The crude was then used in the next step without any further purification. (ES+) m/z 548 (M+H)+

Workup

extractionbefore extracting with EtOAc (2×)
washThe combined organic fractions were washed with brine
dry with materialbefore being dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude was then used in the next step without any further purification

Sources & evidence

ORD record: ord-8731e73dab154f8398b680a224a1e837
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781422B2

Reaction notes

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