Water → HCID 71060529, compound

HRID 1036738Notes

Reaction equation

HRID 1036738 reaction equation
O=C1CCC(=O)N1[C:8](=[O:20])[C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH3:10].[NH2:21][C@H:22]([C@@H:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:27])[C:23]([OH:25])=[O:24].O>C1COCC1>[CH2:29]([O:28][C@@H:26]([CH3:27])[C@@H:22]([NH:21][C:8](=[O:20])[C:9]([NH:12][C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])([CH3:11])[CH3:10])[C:23]([OH:25])=[O:24])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22869571O-Benzyl-D-threonineHCID 71060486Tert-butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-methyl-1-oxopropan-2-ylcarbamate

Product 1

HCID 71060529HCID 71060529, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture comprising of tert-butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-methyl-1-oxopropan-2-ylcarbamate (1 g, 3.33 mmol) (prepared according to the procedure described in EP1486498A1 page 20) and (2R,3S)-2-amino-3-(benzyloxy)butanoic acid (0.697 g, 3.33 mmol) in THF (40 ml)/water (10 ml) was treated with TEA (1.392 ml, 9.99 mmol) and stirred at 50° C. for 4 hours. The resulting mixture was concentrated in vacuo and EtOAc (20 ml) was added. The pH was adjusted to pH2 with 1M HCl. The organic portion was separated and the aqueous phase was back extracted with EtOAc (30 ml). The combined organic portions were washed with a saturated solution of brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in DCM and concentrated in vacuo to afford the title compound.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo and EtOAc (20 ml)
  2. additionwas added
  3. customThe organic portion was separated
  4. extractionthe aqueous phase was back extracted with EtOAc (30 ml)
  5. washThe combined organic portions were washed with a saturated solution of brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in DCM
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4bac0c5cb0548f7a485dab0aeaa5f6d
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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