Sodium Carbonate → HCID 70170719, compound

HRID 2306275Notes

Reaction equation

HRID 2306275 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[CH:7][CH:8]=2)[C:3]=1[N:20]1[CH2:24][CH2:23][C@H:22]([NH:25]C(OC(C)(C)C)=O)[C:21]1=[O:33].C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:25][C@H:22]1[CH2:23][CH2:24][N:20]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[C:6]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15])[CH:5]=3)[CH:10]=[CH:11][C:2]=2[Br:1])[C:21]1=[O:33]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 70170725HCID 70170725, compound

Product 1

HCID 70170719HCID 70170719, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-1-[2-Bromo-7-(tert-butyldimethylsilyloxy)naphthalen-1-yl]-3-(tert-butoxycarbonylamino)-2-oxopyrrolidine, as described above in Step I, (245 mg, 0.458 mmol) was dissolved in a 10% TFA solution in CH2Cl2 (5 mL). After 30 min, the mixture was poured into saturated aqueous Na2CO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient of CH2Cl2—1% to 4% MeOH—0.1% to 0.4% NH4OH, to yield the above-titled compound.

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluting with a gradient of CH2Cl2—1% to 4% MeOH—0.1% to 0.4% NH4OH

Sources & evidence

ORD record
ord-b234c72e40fc440d855ebd0593349095
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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