tert-Butanol → HCID 68692696, compound

HRID 2238437Notes

Reaction equation

HRID 2238437 reaction equation
[CH2:1]([N:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[S:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18](C(O)=O)=[CH:19]2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])=CC=1.CC[N:51]([CH2:54]C)CC.[CH3:56][C:57]([OH:60])([CH3:59])[CH3:58]>>[CH2:25]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[S:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([NH:51][C:54](=[O:39])[O:60][C:57]([CH3:59])([CH3:58])[CH3:56])=[CH:19]2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 44549142HCID 44549142, compound

Product 1

HCID 68692696HCID 68692696, compoundYield 62%

Procedure

A solution of 210 (1.95 g, 4.52 mmol), DPPA (1.49 g, 5.43 mmol) and Et3N (1.01 g, 9.95 mmol) in t-BuOH (40 mL) was heated at reflux for 15 h. The solvents were removed under reduced pressure and the residue purified by chromatography on silica gel, eluting with petroleum ether/EtOAc (4:1), to give tert-butyl 7-[(dibenzylamino)sulfonyl]-2-naphthylcarbamate (211) (1.37 g, 62%). A sample was recrystallised from Et2O/petroleum ether as colorless needles: mp 139-140° C.; 1H NMR (CDCl3) δ8.51 (d, J=1.2 Hz, 1H), 8.03 (d; J=1.3 Hz, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.82 (d, J=8.9 Hz, 1H), 7.68 (dd, J=8.6, 1.8 Hz, 1H), 7.57 (dd, J=8.8, 2.1 Hz, 1H), 7.22-7.12 (m, 6H), 7.08-7.01 (m, 4H), 6.75 (s, 1H), 4.37 (s, 4H), 1.56 (s, 9H); 13C NMR δ 152.1, 137.7, 137.0, 135.1, 132.5, 130.6, 128.5, 128.2, 128.1, 127.9, 127.2, 127.1, 121.3, 120.6, 114.9, 80.6, 50.1, 27.8. Anal. (C29H30N2O4S) C, H, N.

Workup

  1. temperatureat reflux for 15 h
  2. customThe solvents were removed under reduced pressure
  3. customthe residue purified by chromatography on silica gel
  4. washeluting with petroleum ether/EtOAc (4:1)

Sources & evidence

ORD record
ord-5ceb5036d5194e0b8d0d6bc6ca363ef5
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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