Phenol → HCID 21077868, compound

HRID 1374741Notes

Reaction equation

HRID 1374741 reaction equation
N(C(OCC)=O)=N[C:3]([O:5]CC)=[O:4].[OH:13][CH2:14][CH2:15][CH:16]1[CH2:21][N:20]([C:22]([O:24][CH3:25])=[O:23])[CH2:19][CH2:18][NH:17]1.[C:26]1(O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P([C:46]2[CH:51]=[CH:50]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[CH2:53]Cl>>[C:51]([O:5][C:3]([N:17]1[CH2:18][CH2:19][N:20]([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH:16]1[CH2:15][CH2:14][O:13][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:4])([CH3:50])([CH3:46])[CH3:53]

Participants

6

Reactant 5

HCID 996PhenolHCID 6344Dichloromethane2×HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 84046672HCID 84046672, compound

Product 1

HCID 21077868HCID 21077868, compoundYield 84%

Procedure

A solution of diethyl azodicarboxylate (0.74 ml, 4.7 mmol) in anhydrous dichloromethane (3 ml) was added to a stirred, ice-methanol cooled solution of (RS)-1-tert-butoxycarbonyl)-2-(2-hydroxyethyl)-4-methoxycarbonylpiperazine (D7) (1.35 g, 4.69 mmol), phenol (0.441 g, 4.69 mmol) and triphenylphosphine (1.23 g, 4.69 mmol) in anhydrous dichloromethane (40 ml). The mixture was stirred at room temperature for 18 h then evaporated in vacuo. The residue was chromatographed on silica gel eluting with 10–20% ethyl acetate in hexane to give the title compound (1.43 g, 84%). 1H NMR (CDCl3) δ: 1.38 (9H, m), 1.85–2.20 (2H, m), 2.75–3.20(3H, m), 3.72 (3H, s), 3.80–4.20 (5H, m), 4.39 (1H, broad m), 6.75–7.00 (3H, m), 7.15–7.35 (2H, m).

Workup

  1. customthen evaporated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with 10–20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b821133172754d2695b46481f667ed69
Source dataset
uspto-grants-2007_01
Patent number
US07166608B2

Reaction notes

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