Water → HCID 178451016, compound

HRID 1976710Notes

Reaction equation

HRID 1976710 reaction equation
[OH:1][PH:2]([CH2:4][CH:5]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[O:3].[C:22](O)([CH3:25])([CH3:24])[CH3:23].C(N=C=NCCCN(C)C)C.O>ClCCl.CN(C)C1C=CN=CC=1>[C:22]([O:3][PH:2]([CH2:4][CH:5]([CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])=[O:1])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178451017HCID 178451017, compound

Product 1

HCID 178451016HCID 178451016, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-tert-butyl 2-[(hydroxy-phosphinyl)methyl]pentane-1,5-dioate (315 g, 0.977 mol) in dichloromethane (1000 ml) cooled in an ice bath and under nitrogen were added tert-butanol (123.1 g, 1.66 mol), 4-dimethylaminopyridine (1 g, 8.2 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (281 g, 1.47 mol). The reaction was allowed to stir overnight. Water was added to the reaction mixture and the dichloromethane layer was retained and dried, and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography and the desired product was eluted with 1:1 to 2:3 hexane/ethyl acetate. The fractions containing product were concentrated under reduced pressure leaving a clear oil (260 g, 70%). 1H NMR (CDCl3) : δ 1.4 (m, 27H), 1.8 (m, 1H), 1.9 (m, 2H), 2.1 (m, 1H), 2.3 (m, 2H), 2.7-2.8 (m, 1H), 6.7 & 8.0 (d, 1H, the P-H).

Workup

  1. customdried
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting residue was purified by column chromatography
  4. washthe desired product was eluted with 1:1 to 2:3 hexane/ethyl acetate
  5. additionThe fractions containing product
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-cd97090f4ee54efbb2994379c1d992c5
Source dataset
uspto-grants-2001_05
Patent number
US06228888B1

Reaction notes

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