Benzyl Alcohol → benzyl N-(6-hydroxynaphthalen-2-yl)carbamate

HRID 2115749Notes

Reaction equation

HRID 2115749 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](C(O)=O)[CH:6]=[CH:5]2.C[C@H]1[C@]2(O)[C@H]3[C@](O)(CC(COC(C)=O)=C[C@H]2[C@@H]2C(C)(C)[C@]2(O[C:43](CC2C=CC=CC=2)=[O:44])C1)C(=O)C(C)=C3.[CH2:52]([OH:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.CC[N:62](CC)CC>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([NH:62][C:43]([O:59][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:44])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 855576-Hydroxy-2-naphthoic acidHCID 303482112-Deoxyphorbol 13-phenylacetate 20-acetate

Product 1

HCID 67520229benzyl N-(6-hydroxynaphthalen-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Hydroxy-2-naphthoic acid (30 g, 160 mmol, Aldrich), dppa (48.4 g, 176 mmol, Aldrich), benzyl alcohol (51.8 g, 480 mmol, Aldrich) and Et3N (32.3 g, 320 mmol, Aldrich) were heated at reflux with toluene (500 mL, Aldrich) for 16 h. After cooling to RT, the volatile portion was removed in vacuo. The resulting brown residue was purified by silica gel column chromatography (40% EtOAc/hexane) to give crude compound, which was further purified by crystallization from 50% EtOAc/Hexane to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 294.2 (M+1). Mass Calc'd for C18H15NO3: 293.11.

Workup

  1. customthe volatile portion was removed in vacuo
  2. customThe resulting brown residue was purified by silica gel column chromatography (40% EtOAc/hexane)
  3. customto give crude compound, which
  4. customwas further purified by crystallization from 50% EtOAc/Hexane

Sources & evidence

ORD record
ord-2a77420cb2c04e7fb1cabab552710727
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

Loading…