Triethylamine → Isobutyl 3-(Tert-Butyldisulfanyl)-1-(1-(Dichlorophosphoryl)Piperidin-4-ylamino)-1-Oxopropan-2-ylcarbamate

HRID 923722Notes

Reaction equation

HRID 923722 reaction equation
[CH:1]([S:4][S:5][CH2:6][CH:7]([NH:17][C:18](=[O:24])[O:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:8](=[O:16])[NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([CH3:3])[CH3:2].[O:25]=[P:26]([Cl:29])(Cl)[Cl:27].[CH3:30]CN(CC)CC>C(Cl)Cl>[C:1]([S:4][S:5][CH2:6][CH:7]([NH:17][C:18](=[O:24])[O:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:8]([NH:9][CH:10]1[CH2:11][CH2:12][N:13]([P:26]([Cl:29])([Cl:27])=[O:25])[CH2:14][CH2:15]1)=[O:16])([CH3:30])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 71572473Isobutyl 3-(Isopropyldisulfanyl)-1-Oxo-1-(Piperidin-4-ylamino)Propan-2-ylcarbamate

Product 1

HCID 87108177Isobutyl 3-(Tert-Butyldisulfanyl)-1-(1-(Dichlorophosphoryl)Piperidin-4-ylamino)-1-Oxopropan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the compound from Example 61 (7.746 g, 18.12 mmol) in DCM (200 ml) at −78° C. was slowly injected POCl3 (1.69 ml, 18.12 mmol) under Ar, followed by the addition of Et3N (7.58 ml, 54.36 mmol). The reaction was stirred at RT for 5 h, concentrated to remove excess base and solvent. The title compound was given as white solid after ISCO purification (50% EtAc/Hexane).

Workup

  1. customat −78° C.
  2. concentrationconcentrated
  3. customto remove excess base and solvent
  4. customafter ISCO purification (50% EtAc/Hexane)

Sources & evidence

ORD record
ord-5ef87538a87f41009d9a52faaf1c9180
Source dataset
uspto-grants-2016_03
Patent number
US09278987B2

Reaction notes

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