Triethylamine → HCID 46865046, compound

HRID 879964Notes

Reaction equation

HRID 879964 reaction equation
C([CH:8]([NH2:24])[CH2:9][CH2:10][NH:11][C:12]([P:14]([O:20][CH:21]([CH3:23])[CH3:22])([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])=[O:13])(OC(C)(C)C)=O.CCN(CC)CC.[O:32]([C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[O:32]([C:39]1[CH:44]=[CH:43][C:42]([S:45]([NH:24][CH2:8][CH2:9][CH2:10][NH:11][C:12]([P:14]([O:16][CH:17]([CH3:18])[CH3:19])([O:20][CH:21]([CH3:22])[CH3:23])=[O:15])=[O:13])(=[O:47])=[O:46])=[CH:41][CH:40]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27947564-Phenoxybenzene-1-sulfonyl chlorideHCID 86661744HCID 86661744, compound

Product 1

HCID 46865046HCID 46865046, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1-Boc-amino-3-[diisopropylphosphonoformamido]propane (0.7 g, 4 mmol) was dissolved in 5 ml TFA. The reaction was stirred for 30 min. The excess of TFA was removed by evaporation in vacuo with toluene. To the residue in 15 ml DCM were added Et3N (5 eq, 2.8 ml, 20 mmol) and 4-phenoxybenzenesulfonyl chloride (1 g, 45 mmol). The reaction was stirred overnight at room temperature. The mixture was washed with 1N HCl; the organic layer was dried over Na2SO4 and the solvent was evaporated. The product was purified by silica gel chromatography [eluent: CHCl3/1-2% MeOH] to yield 1 g (50%) yellow oil.

Workup

  1. customThe excess of TFA was removed by evaporation in vacuo with toluene
  2. stirringThe reaction was stirred overnight at room temperature
  3. washThe mixture was washed with 1N HCl
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe product was purified by silica gel chromatography [eluent: CHCl3/1-2% MeOH]

Sources & evidence

ORD record
ord-ccfd5c26ab00461789e664550ae37afb
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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