1,3,5-Trioxane → HCID 54268323, compound

HRID 504267Notes

Reaction equation

HRID 504267 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[O:33]1COCO[CH2:34]1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[C@@H:15]([CH2:34][OH:33])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 80811,3,5-TrioxaneHCID 81531DiisopropylethylamineHCID 10957844(S)-4-BENZYL-3-(3-PHENYLPROPANOYL)OXAZOLIDIN-2-ONE

Product 1

HCID 54268323HCID 54268323, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalyst2×HCID 6344DichloromethaneSolvent4×

Procedure

1 M of titanium tetrachloride in DCM (43 mL) was added to a solution of intermediate (7b) (12.7 g, 41 mmol) in DCM (150 mL) at 0° C. under nitrogen. After 20 minutes, DIPEA (7.9 mL, 45.2 mmol) was added dropwise at 0° C. After 80 minutes, 1,3,5-trioxane (4.1 g, 45.2 mmol) in DCM (30 mL) was added, followed by a second equivalent of 1 M titanium tetrachloride in DCM after 10 minutes. After 2.5 hours at 0° C., the mixture was quenched with saturated aqueous NH4Cl (150 mL). The product was extracted with water (100 mL) and DCM (3×200 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to yield intermediate (7c), which was used in the next step without further purification.

Workup

  1. waitAfter 80 minutes
  2. waitAfter 2.5 hours at 0° C.
  3. customthe mixture was quenched with saturated aqueous NH4Cl (150 mL)
  4. extractionThe product was extracted with water (100 mL) and DCM (3×200 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a534b5143c3439ca3f2f2f7920c3ce3
Source dataset
uspto-grants-2010_08
Patent number
US07777077B2

Reaction notes

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