Triphenylphosphine → HCID 23000581, compound

HRID 1058222Notes

Reaction equation

HRID 1058222 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:12]=1[CH2:13][N:14]=[N+]=[N-])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:12]=1[CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 23000592HCID 23000592, compound

Product 1

HCID 23000581HCID 23000581, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 629 mg (2.02 mmol) 2-(2-(tert-butoxycarbonylamino)ethyl)-5-chlorobenzyl azide from the previous step in 30.0 mL THF containing 3.1 mL water was added 1.06 g (4.05 mmol) triphenylphosphine and the reaction was stirred at room temperature overnight. The THF was removed in vacuo and the residual aqueous phase extracted with methylene chloride (3×). The organics were combined, washed with brine, dried over sodium sulfate, filtered and concentrated to dryness in vacuo. Flash chromatography on silica gel (linear gradient from 266/10/1 to 200/10/1 of methylene chloride/methanol/concentrated ammonium hydroxide) gave 2-(2-(tert-butoxycarbonylamino)ethyl)-5-chlorobenzyl amine as a colorless oil: 1H NMR (DMSO-d6, 400 MHz): δ 7.45 (d, 1H, J=1.7 Hz), 7.18 (dd, 1H, J=2.1 and 8.2 Hz), 7.12 (d, 1H, J=8.2 Hz), 7.01 (br t, 1H, J=5.2 Hz), 3.73 (s, 2H), 3.07 (dt, 2H, J=6.5 and 7.3 Hz), 2.68 (t, 2H, J=7.4 Hz), 1.36 (s, 9H); MS (Electrospray): M+H=285.1; TLC Rf=0.33 (160/10/1 of methylene chloride/methanol/concentrated ammonium hydroxide).

Workup

  1. customThe THF was removed in vacuo
  2. extractionthe residual aqueous phase extracted with methylene chloride (3×)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-84581b8e1716429081d0a95c50f65279
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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