Piperidine → (S)-tert-Butyl 2-(2-amino-3-(4-hydroxyphenyl)propanamido)acetate

HRID 1755481Notes

Reaction equation

HRID 1755481 reaction equation
C1C2C(COC([NH:18][C@@H:19]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)[C:20]([NH:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[NH2:18][C@@H:19]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)[C:20]([NH:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])=[O:21]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86700124(S)-tert-Butyl 2-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-hydroxyphenyl)propanamido)acetate

Product 1

HCID 86700125(S)-tert-Butyl 2-(2-amino-3-(4-hydroxyphenyl)propanamido)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution material from Example 97 (4.7 g, 9.10 mmol) in anhydrous DMF (30 mL) is added piperidine (15 mL, 152 mmol). The resulting solution is stirred at room temp for 45 rain and the solvent is removed in vacuo. The resulting residue was redissolved in 1,4-dioxane (50 mL), the solvent was removed in vacuo again and the resulting solid was dried under high vacuum for 18 h to give the title compound as a white solid in quantitative yield that contains 1 equivalent of 1-((9H-fluoren-9-yl)methyl)piperidine as a side product. LC/MS (Condition A): ret. T=2.30 rain, (M+H)+ 295.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe resulting residue was redissolved in 1,4-dioxane (50 mL)
  3. customthe solvent was removed in vacuo again
  4. customthe resulting solid was dried under high vacuum for 18 h

Sources & evidence

ORD record
ord-501da06283154387a78b5e9bdd6f2590
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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