Trimethylphosphine → HCID 68283999, compound

HRID 1527390Notes

Reaction equation

HRID 1527390 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][N:15]=[N+]=[N-])([F:13])[CH2:10][C@H:9]1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].P(C)(C)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][NH2:15])([F:13])[CH2:10][C@H:9]1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[F:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 86673837HCID 86673837, compound

Product 1

HCID 68283999HCID 68283999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,4R)-4-azidomethyl-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (380 mg, 0.884 mmol) in THF (25 mL) under N2 atmosphere at RT was added 1M PMe3 in THF (1.06 mL, 1.06 mmol). The reaction mixture was stirred for 16 h then quenched with water and extracted twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (CH2Cl2/MeOH 8:2) to give the desired material. MS (LC/MS): 404/406 [M+H]+, 402 [M−H]−; tR (HPLC conditions f): 1.57 min, 19F NMR (100 MHz, DMSO-d6) δ (ppm): −120, −154.

Workup

  1. customthen quenched with water
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography on silica gel (CH2Cl2/MeOH 8:2)

Sources & evidence

ORD record
ord-5beb18ab236a44738709cdefb9a051ab
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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