Hydrochloric Acid → 3-Amino-2,2-dimethyl-propionic acid TFA salt

HRID 1481150Notes

Reaction equation

HRID 1481150 reaction equation
C[O:2][C:3](=[O:16])[C:4]([CH3:15])([CH3:14])[CH2:5][NH:6]C(OC(C)(C)C)=O.[OH-].[Na+].Cl.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]>CO.C(Cl)Cl>[OH:26][C:20]([C:22]([F:25])([F:24])[F:23])=[O:21].[NH2:6][CH2:5][C:4]([CH3:15])([CH3:14])[C:3]([OH:16])=[O:2]

Participants

7

Procedure

To a solution of 3-tert-butoxycarbonylamino-2,2-dimethyl-propionic acid methyl ester (2.5 g, 10.8 mmol) in MeOH (30 mL) was added 1 M NaOH (27 mL, 27 mmol), and the resulting mixture was stirred at r.t. for 16 h. 1 M HCl was added until pH was ˜3, and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The residue obtained was dissolved CH2Cl2 (10 mL), and TFA (7 mL) was added. The resulting mixture was stirred at r.t. for 3 days, then concentrated to dryness to give 2.1 g of the title compound as a gray solid. 1H NMR (DMSO-d6, 200 MHz): δ ppm=7.8 (br s, 3H), 2.80-3.00 (m, 2H), 1.18 (s, 6H).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue obtained
  5. additionwas added
  6. stirringThe resulting mixture was stirred at r.t. for 3 days
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-fa98b959a7ec4d7fad1f4089dcda8fb0
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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