Dichloromethane → HCID 67383174, compound

HRID 335968Notes

Reaction equation

HRID 335968 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:28]=1)[C:18]1[CH:17]=[C:16]([O:19]C)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([N:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])=[CH:9][C:10]=1[F:21].C(Cl)Cl>>[NH2:1][C:2]1[O:3][CH2:4][C@:5]2([N:28]=1)[C:18]1[CH:17]=[C:16]([OH:19])[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([N:22]2[CH2:26][CH2:25][CH2:24][C:23]2=[O:27])=[CH:9][C:10]=1[F:21]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 67383100HCID 67383100, compound

Product 1

HCID 67383174HCID 67383174, compound

Procedure

To a solution of (S)-1-(2-amino-5′-fluoro-2′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)pyrrolidin-2-one (377 mg, 0.98 mmol) in DCM (6 mL) boron tribromide (0.2 mL, 2.46 mmol) was added at 0° C. The bath was removed and the mixture was allowed to warm up to RT and stirred for 30 min. The reaction was quenched with sat NaHCO3 and diluted with DCM. The insoluble material was dissolved by adding MeOH. Organic layer was filtered through celite and concentrated to afford (S)-1-(2-amino-5′-fluoro-2′-hydroxy-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)pyrrolidin-2-one.

Workup

  1. customThe bath was removed
  2. customThe reaction was quenched with sat NaHCO3
  3. additiondiluted with DCM
  4. dissolutionThe insoluble material was dissolved
  5. additionby adding MeOH
  6. filtrationOrganic layer was filtered through celite
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-91e74e5bcb6749f4be527a13e5f46a0e
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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