Hydrochloric Acid → HCID 118318816, compound

HRID 921138Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:10]1[C:37]([CH3:38])=[N:36][C:35]2=[CH:39][C:32]3=[N:33][N:34]2[C:11]=1[N:12]1[CH2:43][CH2:42][C:15]([CH3:44])([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([CH3:41])[O:22][C:23]2[CH:24]=[C:25]([CH3:40])[CH:26]=[CH:27][C:28]=2[CH2:29][O:30][CH2:31]3)[CH2:14][CH2:13]1)[C:7]([O-:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C@@H:6]([C:10]1[C:37]([CH3:38])=[N:36][C:35]2=[CH:39][C:32]3=[N:33][N:34]2[C:11]=1[N:12]1[CH2:13][CH2:14][C:15]([CH3:44])([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([CH3:41])[O:22][C:23]2[CH:24]=[C:25]([CH3:40])[CH:26]=[CH:27][C:28]=2[CH2:29][O:30][CH2:31]3)[CH2:42][CH2:43]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

(2S)-2-(tert-Butoxy)-2-[(20S)-4,16,20,26-tetramethyl-11,19,25-trioxa-1,5,7,8-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl]acetate (22 mg, 0.035 mmol) was dissolved in MeOH (1 mL). To this was added 1N sodium hydroxide (0.138 mL, 0.138 mmol) and the mixture heated to 60° C. (oil bath temperature). After stirring for 3 hrs the mixture was transferred to a separatory funnel and acidified with 1N HCl. The solution was then extracted with ethyl acetate and the organic layer dried over Na2SO4. After filtration the solvent was removed to under vacuum to provide 24 mg of the title compound as a powder. LCMS (M+H)=609.2.

Workup

customwas transferred to a separatory funnel
extractionThe solution was then extracted with ethyl acetate
dry with materialthe organic layer dried over Na2SO4
filtrationAfter filtration the solvent
customwas removed to under vacuum

Sources & evidence

ORD record: ord-c49489e423d740339169581745eb1c71
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

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