Water → HCID 68283350, compound

HRID 1527395Notes

Reaction equation

HRID 1527395 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([C:14](C)(C)[O:15][SiH2]C(C)(C)C)([F:13])[CH2:10][C@H:9]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:13])([CH2:14][OH:15])[CH2:10][C@H:9]1[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131733203HCID 131733203, compound

Product 1

HCID 68283350HCID 68283350, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,4R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-fluoro-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (4.10 g, 8.77 mmol) in THF (80 mL) at RT was added 1M TBAF in THF (17.53 mL, 17.53 mmol). The reaction was stirred at RT for 30 min then poured into water and extracted with EtOAc. The organic layer was dried with Na2SO4, filtered and concentrated. Purification by flash column chromatography on silica gel (c-hexane/EtOAc 3:2). MS (UPLC/MS): 354 [M+H]+, 398 [M+HCOO]−; tR (HPLC conditions f): 2.07 min.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (c-hexane/EtOAc 3:2)
  6. custom2.07 min.

Sources & evidence

ORD record
ord-be443cf55e7641368ceed220a6f5508d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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