Ethyl Acetate → HCID 86706784, compound

HRID 710071Notes

Reaction equation

HRID 710071 reaction equation
CCOC(C)=O.[OH:7][N:8]=[CH:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].CN1C(=O)CCC1.C1C(=O)N([Cl:36])C(=O)C1>O>[Cl:36][C:9](=[N:8][OH:7])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 31398ChlorosuccinimideHCID 86706742HCID 86706742, compound

Product 1

HCID 86706784HCID 86706784, compoundYield 294.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an AcOEt (270 ml) solution of the (S)-t-butyl 2-((hydroxyimino)methyl)pyrrolidine-1-carboxylate (32.0 g) obtained in Example 2-(1), NMP (43.1 ml) was added and after adding NCS (21.94 g) in three divided portions at 20- to 30-min intervals at 30 to 40° C., the resulting mixture was stirred at room temperature for 0.5 hour. The same reaction was carried out in a total of four runs using the same quantities. To the reaction mixture, water (400 ml) was added and the organic layer was separated. The separated organic layers were combined, washed with water (1.2 L×2), dried (MgSO4), filtered and concentrated to give a crude product (pale yellow solid, 174 g), which was washed with AcOEt/hexane (AcOEt/hexane=140 ml/840 ml) and dried to give the titled compound (109.3 g, colorless solid.)

Workup

  1. customThe same reaction
  2. customthe organic layer was separated
  3. washwashed with water (1.2 L×2)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product (pale yellow solid, 174 g), which
  8. washwas washed with AcOEt/hexane (AcOEt/hexane=140 ml/840 ml)
  9. customdried

Sources & evidence

ORD record
ord-370d1406e5b84bafb0eb077e08ecf455
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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