(R)-tert-butyl 1-amino-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate → (R)-2-amino-3-(thiophen-2-yl)propanamide

HRID 2201124Notes

Reaction equation

HRID 2201124 reaction equation
[NH2:1][C:2](=[O:18])[C@H:3]([NH:10]C(=O)OC(C)(C)C)[CH2:4][C:5]1[S:6][CH:7]=[CH:8][CH:9]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:10][C@H:3]([CH2:4][C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[C:2]([NH2:1])=[O:18]

Participants

4

Reactant 1

HCID 67776928(R)-tert-butyl 1-amino-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

Product 1

HCID 67508269(R)-2-amino-3-(thiophen-2-yl)propanamideYield 32.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-tert-butyl 1-amino-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (454 mg, 1.68 mmol) in TFA (4 mL) and CH2Cl2 (6 mL) was stirred at room temperature for 3 h. It was then concentrated in vacuo. The residue was partitioned between EtOAc and aq. 5% NaHCO3. The EtOAc phase was separated, washed with water, concentrated in vacuo to give (R)-2-amino-3-(thiophen-2-yl)propanamide (93 mg).

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customThe residue was partitioned between EtOAc and aq. 5% NaHCO3
  3. customThe EtOAc phase was separated
  4. washwashed with water
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0985772c13014cd7bc7bbe25dc992065
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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