Hydrochloric Acid → (2S)-2-amino-1-(benzo[d]oxazol-2-yl)butan-1-ol dihydrochloride

HRID 1025322Notes

Reaction equation

HRID 1025322 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:22])[C@@H:11]([NH:14]C(=O)OC(C)(C)C)[CH2:12][CH3:13].[ClH:23]>O1CCOCC1>[ClH:23].[ClH:23].[NH2:14][C@@H:11]([CH2:12][CH3:13])[CH:10]([C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)[OH:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11522383tert-butyl (2S)-1-(benzo[d]oxazol-2-yl)-1-hydroxybutan-2-ylcarbamate

Product 1

HCID 86762432(2S)-2-amino-1-(benzo[d]oxazol-2-yl)butan-1-ol dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Under an atmosphere of argon, tert-butyl (2S)-1-(benzo[d]oxazol-2-yl)-1-hydroxybutan-2-ylcarbamate (800 mg, 2.61 mmol, Eq: 1.00) and HCl 4M in dioxane (17.3 ml) were combined to give a dark brown solution. The reaction was stirred for 2 h at RT. The crude reaction mixture was concentrated in vacuo, and the residual solvent was removed under vacuum. The title compound was obtained as a dark brown gum (910 mg, quant., MS (m/e)=207.1 [M+H+]).

Workup

  1. customto give a dark brown solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residual solvent was removed under vacuum

Sources & evidence

ORD record
ord-e70eba47d28c4d449340b270008570de
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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