Triphenylphosphine → Methyl 3-[2-[2-(tritylamino)ethoxy)phenyl]propionate

HRID 481001

Reaction equation

HRID 481001 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([NH:32][CH2:33][CH2:34][OH:35])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:13]([NH:32][CH2:33][CH2:34][O:35][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2794569Methyl 3-(2-hydroxyphenyl)propionateHCID 31256082-((Triphenylmethyl)amino)ethanol

Product 1

HCID 18765898Methyl 3-[2-[2-(tritylamino)ethoxy)phenyl]propionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (4.2 ml, 26.4 mmol) was added to a mixture of 2-(tritylamino)ethanol (6.08 g, 20.0 mmol), methyl 3-(2-hydroxyphenyl)propionate (5.00 g, 26.4 mmol), triphenylphosphine (6.91 g, 30.5 mmol) and THF (90 ml) at room temperature under nitrogen, and the mixture was standing for 20 hours at room temperature. The solvent was removed in vacuum. The residue was purified on SiO2, eluting with ethyl acetate-hexane (1:15), to afford the titled product as a colorless oil. (5.88 g, 49%)

Workup

  1. customThe solvent was removed in vacuum
  2. customThe residue was purified on SiO2
  3. washeluting with ethyl acetate-hexane (1:15)

Sources & evidence

ORD record
ord-6b4aafe92c4d4ba099784bdb87349e3f
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Linked notes

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