tert-Butanol → HCID 44549528, compound

HRID 2238405Notes

Reaction equation

HRID 2238405 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10](C(O)=O)[CH:9]=[CH:8]2)(=[O:4])=[O:3].CC[N:20]([CH2:23]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])=CC=1.[CH3:42][C:43]([OH:46])([CH3:45])[CH3:44]>>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([NH:20][C:23](=[O:32])[O:46][C:43]([CH3:45])([CH3:44])[CH3:42])[CH:9]=[CH:8]2)(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 44550984HCID 44550984, compound

Product 1

HCID 44549528HCID 44549528, compoundYield 87%

Procedure

A suspension of acid 160 (4.08 g, 16.30 mmol) in dry t-BuOH (70 mL) containing powdered molecular sieves (2 g) was treated with Et3N (2.73 mL, 19.59 mmol) and stirred under N2 at room temperature for 30 min. DPPA (3.87 mL, 17.96 mmol) was added and the mixture was stirred at reflux for 6 h, then concentrated to a small volume under reduced pressure and poured into dilute aqueous NaHCO3. The resulting solid was purified by chromatography on silica gel, eluting with CH2Cl2, to give tert-butyl 6-(methylsulfonyl)-2-naphthylcarbamate (161) (4.57 g, 87%) as a white solid: mp (EtOAc/hexane) 203-204° C.; 1H NMR [(CD3)2SO] δ 9.81 (s, 1H); 8.44 (d, J=1.2 Hz, 1H), 8.26 (s, 1H), 8.08 (d, J=9.0 Hz, 1H), 8.01 (d, J=8.7 Hz, 1H), 7.84 (dd, J=8.7, 1.8 Hz, 1H), 7.66 (dd, J=8.9, 2.0 Hz, 1H), 3.25 (s, 3H), 1.52 (s, 9H). Anal. (C16H19NO4S) Cl, N.

Workup

  1. additioncontaining
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 6 h
  4. concentrationconcentrated to a small volume under reduced pressure
  5. additionpoured into dilute aqueous NaHCO3
  6. customThe resulting solid was purified by chromatography on silica gel
  7. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-a8e4578eeb184626a82c78cafccacf72
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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