Phosphinecarboxylic acid, bis(1-methylethoxy)-, 4-nitrophenyl ester, oxide → HCID 86661746, compound

HRID 879969Notes

Reaction equation

HRID 879969 reaction equation
[N+](C1C=CC([O:8][C:9]([P:11](=[O:20])([O:16][CH:17]([CH3:19])[CH3:18])[O:12][CH:13]([CH3:15])[CH3:14])=O)=CC=1)([O-])=O.[C:23]1([C:29]([NH:42][C@@H:43]([CH2:46][NH2:47])[CH2:44][OH:45])([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH:13]([O:12][P:11]([C:9]([NH:47][CH2:46][C@H:43]([NH:42][C:29]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:44][OH:45])=[O:8])([O:16][CH:17]([CH3:19])[CH3:18])=[O:20])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 512122Phosphinecarboxylic acid, bis(1-methylethoxy)-, 4-nitrophenyl ester, oxideHCID 10806499HCID 10806499, compound

Product 1

HCID 86661746HCID 86661746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of diisopropyl 4-nitrophenoxycarbonylphosphonate (i-Pr-NPPF) (9.27 g, 28 mmol) in dry CH2Cl2 (50 mL) was added dropwise to a solution of (S)-2-triphenylmethylamino-3-aminopropanol (9.3 g, 28 mmol) in dry CH2Cl2 (100 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 h. Workup was done by washing the reaction mixture successively with 0.5 M NaOH and water. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue obtained was purified by column chromatography (silica gel, 70% EtOAc in pet. ether) to provide (S)-3-diisopropylphosphonoformamido-2-(tritylamino)propanol as gummy solid in 82% (12.0 g) yield.

Workup

  1. washby washing the reaction mixture successively with 0.5 M NaOH and water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customwas purified by column chromatography (silica gel, 70% EtOAc in pet. ether)

Sources & evidence

ORD record
ord-d9a0fb8980944022815b6e60059696b9
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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