Hydrochloric Acid → HCID 19605568, compound

HRID 1603950Notes

Reaction equation

HRID 1603950 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([NH:17]C(OC(C)(C)C)=O)[CH:14]=[CH:13][C:5]=1[O:6][CH2:7][C:8]([O:10]CC)=[O:9])([O-:3])=[O:2].Cl.[CH3:26][CH2:27]OC(C)=O>>[CH2:26]([CH:7]([O:6][C:5]1[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:4]=1[N+:1]([O-:3])=[O:2])[C:8]([OH:10])=[O:9])[CH3:27]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 19605580HCID 19605580, compound

Product 1

HCID 19605568HCID 19605568, compound

Conditions

Temperature
0 °C

Procedure

A solution of 5-2 (0.3 g, 0.88 mmol) was dissolved in EtOAc (10 mL), cooled to -78° C. and saturated with HCl gas, warmed to 0° C. for 1 hour and concentrated to give ethyl 2-(2-nitro-4-aminophenoxy)acetic acid as a white solid that was coupled immediately (0.26 g, 0.88 mmol) to 1-5 (0.29 g, 0.95 mmol) as described for 5--5 to give 5-9 as a yellow solid after chromatography in a gradient of 40 to 100% EtOAc/hexanes.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-78bddd3b2ada47ddbf76b1a35d1a87a9
Source dataset
uspto-grants-1999_11
Patent number
US05990107

Reaction notes

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