Tetrahydrofuran → HCID 69556662, compound

HRID 479136Notes

Reaction equation

HRID 479136 reaction equation
C([C@H]1COC(=O)N1C(=O)[C@@H:15]([O:46][CH3:47])[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([O:27][CH2:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:19][CH:18]=1)C1C=CC=CC=1.[OH-:49].[Na+].C1[CH2:55][O:54]CC1>>[CH3:47][O:46][C@@H:15]([CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([O:27][CH2:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:37]=[CH:38][C:39]([C:42]([F:44])([F:45])[F:43])=[CH:40][CH:41]=3)[O:33][C:34]=2[CH3:35])=[CH:19][CH:18]=1)[C:55]([OH:54])=[O:49]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69556698HCID 69556698, compound

Product 1

HCID 69556662HCID 69556662, compound

Procedure

0.698 g of the above prepared (S)-4-benzyl-3-[(S)-2-methoxy-3-(4-{2-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-ethoxy}-naphthalen-1-yl)-propionyl]-oxazolidin-2-one (1.03 mmol) was dissolved in 7.5 ml of THF and treated with 2.57 ml of 1N NaOH (2.5 eq.). The reaction mixture was kept at 0° and progress of the hydrolysis followed by TLC. After 1 h the reaction mixture was poured onto crashed ice and extracted with ether to remove the chiral auxiliary. The aqueous layer was then acidified with HCl, extracted twice with AcOEt, washed with water, dried over magnesium sulfate, and evaporated to dryness. Crystallization from AcOEt yielded finally 0.356 g of the title product as white crystals of mp. 167-68°.

Workup

  1. customwas kept at 0°
  2. additionAfter 1 h the reaction mixture was poured
  3. extractionextracted with ether
  4. customto remove the chiral auxiliary
  5. extractionextracted twice with AcOEt
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness
  9. customCrystallization from AcOEt

Sources & evidence

ORD record
ord-a4afe4ab292645e3a60cee5f715ee473
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

Loading…