Triphenylphosphine → Methyl N-isobutyryl-O-{2-[4-(methoxymethyl)phenyl]ethyl}tyrosinate

HRID 987140Notes

Reaction equation

HRID 987140 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.[C:13]([NH:18][C@H:19]([C:28]([O:30][CH3:31])=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1)(=[O:17])[CH:14]([CH3:16])[CH3:15].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:13]([NH:18][C@H:19]([C:28]([O:30][CH3:31])=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][O:2][CH3:1])=[CH:5][CH:6]=2)=[CH:23][CH:22]=1)(=[O:17])[CH:14]([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 229884104-(Methoxymethyl)phenethyl alcoholHCID 69905890methyl N-isobutyryltyrosinate

Product 1

HCID 21364621Methyl N-isobutyryl-O-{2-[4-(methoxymethyl)phenyl]ethyl}tyrosinateYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[4-(Methoxymethyl)phenyl]ethanol (0.6 g, 3.61 mmol) and methyl N-isobutyryltyrosinate (1.15 g, 4.34 mmol) were mixed in dichloromethane (20 ml, dry). 1,1′-(Azodicarbonyl)dipiperidine (1.1 g, 4.36 mmol) and triphenylphosphine (1.14 g, 4.35 mmol) were then added respectively. The mixture was stirred at room temperature overnight and filtered. The filtrate was evaporated in vacuum to dry. Column chromatography of the residue on silica gel using ethyl acetate/heptane (gradient 5:95 to 50:50) as eluant gave 0.71 g desired product, yield 48%.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuum
  3. customto dry

Sources & evidence

ORD record
ord-365f837f1f2c46a8a6488f13ff6206a4
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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