Hydrochloric Acid → HCID 118045649, compound

HRID 595970Notes

Reaction equation

HRID 595970 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:14]C(=O)OC(C)(C)C)[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([Br:13])[CH:7]=1)=[N+:2]=[N-:3].[ClH:22]>O1CCOCC1>[ClH:22].[N:1]([CH2:4][C@H:5]([C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([Br:13])[CH:7]=1)[NH2:14])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118054599HCID 118054599, compound

Product 1

HCID 118045649HCID 118045649, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of (S)-tert-butyl (2-azido-1-(3-bromo-5-fluorophenyl)ethyl)carbamate (3.15 g, 8.77 mmol) in dioxane (40 mL) was added hydrochloric acid (10.96 mL, 43.8 mmol) (4N solution in dioxane). The reaction was heated to 40° C. and maintained at this temperature for 2 h. After cooling the reaction mixture was evaporated to dryness, giving (S)-2-azido-1-(3-bromo-5-fluorophenyl)ethanamine hydrochloride (2.59 g, 8.76 mmol, 100% yield) as a white solid.

Workup

  1. temperaturemaintained at this temperature for 2 h
  2. temperatureAfter cooling the reaction mixture
  3. customwas evaporated to dryness

Sources & evidence

ORD record
ord-529c43a486004bc6a966e1371dca2efc
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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