Diethyl Ether → HCID 68608925, compound

HRID 643094Notes

Reaction equation

[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12](=[O:16])[C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[CH3:17].C(N(CC)CC)C.[OH-].[Na+].C(OCC)C>C1COCC1>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C@@H:12]([OH:16])[C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[CH3:17]

Participants

Conditions

Temperature: -35 °C

Procedure

Under a nitrogen atmosphere a solution of 12.0 g (37.4 mmol) (1R)-B-chlorodiisopinocampheylborane in 40 mL THF was added dropwise within 15 min to a solution of 6.5 g (26.0 mmol) 3-(4-amino-3-methyl-5-nitro-phenyl)-2-oxo-propionic acid and 4.5 mL (32.4 mmol) triethylamine in 100 mL THF cooled to −35° C. and the reaction solution was stirred overnight at RT. Then the reaction solution was carefully combined with 60 mL 1 M NaOH and 150 mL diethyl ether at 5° C. and stirred for 15 min. The organic phase was separated off, extracted three times with 40 mL 1 M NaOH and once with 40 mL water. The combined aqueous phases were acidified with semiconc. HCl while cooling with an ice bath and extracted twice with 120 mL EtOAc in each case. The combined organic phases were dried over Na2SO4 and evaporated down i.vac. The crude product was obtained, which was further reacted without purification.

Workup

stirringstirred for 15 min
customThe organic phase was separated off
extractionextracted three times with 40 mL 1 M NaOH
temperatureHCl while cooling with an ice bath
extractionextracted twice with 120 mL EtOAc in each case
dry with materialThe combined organic phases were dried over Na2SO4
customevaporated down i.vac

Sources & evidence

ORD record: ord-bf07aec5cb93441585575484d85c9490
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696209B2

Reaction notes

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