(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acid benzyl ester → (S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acid

HRID 716508Notes

Reaction equation

HRID 716508 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:32])[C@H:17]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:28]([O:27][C:25]([NH:24][C@H:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:32])=[O:26])([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 15288611(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acid benzyl ester

Product 1

HCID 10089106(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acidYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of compound 2a (2 mmol) and Pd/C (20 w %) in ethanol (30 mL) was hydrogenated for 3 hrs at atmospheric pressure. The reaction mixture was filtered off and concentrated in vacuo. The crude was taken in toluene and concentrated again, and then in Et2O/petroleum ether and concentrated once more to give compound 3a as a glassy solid in 62% yield over two steps. MS (ESI, EI−) m/z=347 (MH−).

Workup

  1. filtrationThe reaction mixture was filtered off
  2. concentrationconcentrated in vacuo
  3. concentrationconcentrated again
  4. concentrationin Et2O/petroleum ether and concentrated once more

Sources & evidence

ORD record
ord-87ce17c5956043e5887365d48ceac060
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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