Water → HCID 68283694, compound

HRID 1527406Notes

Reaction equation

HRID 1527406 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+]=[N-])[C@H:10]([F:16])[C@H:9]1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[F:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].CP(C)C.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([NH2:13])[C@H:10]([F:16])[C@H:9]1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[F:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 86673849HCID 86673849, compound

Product 1

HCID 68283694HCID 68283694, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2R,3R,4R)-4-azido-2-(3-chloro-2-fluoro-benzylcarbamoyl)-3-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (described in Scheme B19) (485 mg, 1.16 mmol), trimethylphosphine in THF (2.33 mL, 2.33 mmol) and water (0.04 mL, 2.33 mmol) in THF (20 mL) was stirred for 16 h at RT. The reaction mixture was quenched with water and extracted twice with EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography on silica gel (CH2Cl2/MeOH 95:5). MS (UPLC/MS): 390/392 [M+H]+, 434/436 [M+HCOO]−; tR (HPLC conditions f): 1.64 min.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted twice with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (CH2Cl2/MeOH 95:5)
  8. custom1.64 min.

Sources & evidence

ORD record
ord-54e00643523e42fca2b2087dc880cd0b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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