Triphenylphosphine → HCID 19779532, compound

HRID 2082079Notes

Reaction equation

HRID 2082079 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][C:14]1([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[O:18][CH2:17][CH2:16][O:15]1.[C:28]([O:32][C:33]([NH:35][CH:36](O)[CH3:37])=[O:34])([CH3:31])([CH3:30])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:28]([O:32][C:33]([NH:35][CH2:36][CH2:37][O:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:14]2([CH3:13])[O:18][CH2:17][CH2:16][O:15]2)=[CH:22][CH:23]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 197795284-[(2-Methyl-1,3-dioxolan-2-yl)methoxy]phenolHCID 22620026t-Butoxycarbonylaminoethanol

Product 1

HCID 19779532HCID 19779532, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (3.8 ml) was added dropwise to a stirred solution of 4-[(2-methyl-1,3-dioxolan-2-yl)methoxy]phenol (3.4 g), N-t-butoxycarbonylaminoethanol (5.2 g) and triphenylphosphine (6.3 g) in anhydrous tetrahydrofuran (100 ml), at ice-bath temperature, under argon. The reaction mixture was left for 64 hours at 25° C. and then the solvent was removed under reduced pressure. The residue was dissolved in ether (100 ml) and the ethereal solution washed with 2N aqueous sodium hydroxide (2×50 ml), water (2×50 ml) and saturated brine (50 ml). The aqueous washings were in turn extracted with ether (50 ml). The ethereal solutions were combined, dried, and the ether removed under reduced pressure. The residue was purified by chromatography using 11/2% tetrahydrofuran in dichloromethane as eluent. The appropriate fractions were combined and evaporated to yield 1-t-butoxycarbonylamino-2-[4-((2-methyl-1,3-dioxolan-2-yl)-methoxy)phenoxy]ethane as a light yellow solid (3.2 g) m.p. 80°-82° C. (from cyclohexane); microanalysis: found C, 61.3; H, 7.7; N, 3.8%; required for C18H27NO6 : C, 61.2; H, 7.6; N 4.0%.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ether (100 ml)
  3. washthe ethereal solution washed with 2N aqueous sodium hydroxide (2×50 ml), water (2×50 ml) and saturated brine (50 ml)
  4. extractionextracted with ether (50 ml)
  5. customdried
  6. customthe ether removed under reduced pressure
  7. customThe residue was purified by chromatography
  8. customevaporated

Sources & evidence

ORD record
ord-9988d3fbe2114963be2b3edc790cc57d
Source dataset
uspto-grants-1993_02
Patent number
US05187190

Reaction notes

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