tert-Butanol → HCID 44549669, compound

HRID 2238410Notes

Reaction equation

HRID 2238410 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10](C(O)=O)=[CH:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.CC[N:36]([CH2:39]C)CC.CC[O:43]C(C)=O.[CH3:47][C:48]([OH:51])([CH3:50])[CH3:49]>>[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH:36][C:39](=[O:43])[O:51][C:48]([CH3:50])([CH3:49])[CH3:47])=[CH:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 44549144HCID 44549144, compound

Product 1

HCID 44549669HCID 44549669, compoundYield 62%

Procedure

A solution of acid 169 (550 mg, 2.57 mmol), DPPA (850 mg, 3.08 mmol) and Et3N (570 mg, 5.65 mmol) in t-BuOH (20 mL) was heated under reflux for 15 h. The mixture was poured into EtOAc and filtered through Celite. Chromatography on silica gel eluting with petroleum ether/CH2Cl2/EtOAc (8:1:1) gave tert-butyl 7-acetyl-2-naphthylcarbamate (170) (451 mg, 62%) as a colorless solid: mp (EtOAc) 161-163° C.; 1H NMR (CDCl3) δ 8.38 (br s, 1H), 8.16 (br s, 1H), 7.91 (dd, J=8.5, 1.7 Hz, 1H), 7.80 (d, J=8.6 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.43 (dd, J=8.8, 2.2 Hz, 1H), 6.68 (br s, 1H), 2.70 (s, 3H), 1.55 (s, 9H); 13C NMR δ 198.2, 152.7, 136.7, 135.0, 133.2, 132.0, 1297, 128.5, 128.0, 122.4, 121.6, 115.8, 81.0, 28.3, 26.6. Anal. (C17H19NO3) C, H, N.

Workup

  1. temperatureunder reflux for 15 h
  2. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-174532e8230e4e49a049daf390ed2c73
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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