tert-Butanol → HCID 44549670, compound

HRID 2238414Notes

Reaction equation

HRID 2238414 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11](C(O)=O)=[CH:12]2)=[CH:7][CH:6]=1)=[O:4].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])=CC=1.CC[N:37]([CH2:40]C)CC.[CH3:42][C:43]([OH:46])([CH3:45])[CH3:44]>>[C:43]([O:46][C:40]([NH:37][C:11]1[CH:12]=[C:13]2[C:8]([CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:14]2)=[CH:9][CH:10]=1)=[O:25])([CH3:45])([CH3:44])[CH3:42]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 684813357568-17-4

Product 1

HCID 44549670HCID 44549670, compoundYield 80%

Procedure

A solution of acid 178 (50 mg, 0.22 mmol), DPPA (72 mg, 0.26 mmol) and Et3N (48 mg, 0.48 mmol) in t-BuOH (5 mL) was heated under reflux for 20 h. The solvents were removed under reduced pressure and the residue was purified by chromatography eluting with CH2Cl2/MeOH (49:1) followed by recrystallization (EtOAc/petroleum ether) to give methyl 7-[(tert-butoxycarbonyl)amino]-2-naphthoate (179) (52 mg, 80%) as colorless needles. A sample was recrystallised: mp (CH2Cl2/n-hexane) 181-183° C.; 1H NMR (CDCB) δ 8.52 (br s, 1H), 8.05 (br s, 1H), 7.94 (dd, J=8.5, 1.7 Hz, 1H), 7.79 (d, J=8.7 Hz, 2H), 7.51 (dd, J=8.8, 2.1 Hz, 1H), 6.67 (or s, 1H), 3.97 (s, 3H), 1.56 (s 9H); 13C NMR 167.3, 152.7, 136.6, 133.1, 132.0, 130.4, 128.6, 127.9, 127.8, 123.8, 121.5, 115.6, 80.9, 52.2, 28.3. Anal. (C17H19NO4) C, H, N.

Workup

  1. temperatureunder reflux for 20 h
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was purified by chromatography
  4. washeluting with CH2Cl2/MeOH (49:1)
  5. customfollowed by recrystallization (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-1bf8c82e360048e08d318e94c43cb23b
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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