tert-Butanol → HCID 44549666, compound

HRID 2238430Notes

Reaction equation

HRID 2238430 reaction equation
[CH3:1][S:2]([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])=[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:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([NH:20][C:23](=[O:32])[O:46][C:43]([CH3:45])([CH3:44])[CH3:42])=[CH:12]2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 44550987HCID 44550987, compound

Product 1

HCID 44549666HCID 44549666, compoundYield 79%

Procedure

A suspension of acid 201 (2.08 g, 8.31 mmol) in dry t-BuOH (30 mL) containing powdered molecular sieves (1 g) was treated with Et3N (1.39 mL, 9.97 mmol) and stirred under N2 at room temperature for 30 min. DPPA (1.97 mL, 9.14 mmol) was added and the mixture was stirred at reflux for 7 h, then concentrated to half volume under reduced pressure and poured into dilute aqueous KHCO3. The resulting solid was purified by chromatography on silica gel, eluting with CH2Cl2/EtOAc (19:1), followed by recrystallization from CH2Cl2/iPr2O to give tert-butyl 7-(methylsulfonyl)-2-naphthylcarbamate (202) (2.11 g, 79%) as a white solid: mp 179-180° C.; 1H NMR [(CD3)2SO] δ 9.76 (s, 1H), 8.39 (d, J=1.5 Hz, 1H), 8.28 (d, J=1.5 Hz, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.98 (d, J=9.0 Hz, 1H), 7.77 (dd, J=8.6, 1.9 Hz, 1H), 7.74 (dd, J=9.2, 2.0 Hz, 1H), 3.27 (s, 3H), 1.52 (s, 9H). Anal. (C16H19NO4S) C, H, N.

Workup

  1. additioncontaining
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 7 h
  4. concentrationconcentrated to half volume under reduced pressure
  5. additionpoured into dilute aqueous KHCO3
  6. customThe resulting solid was purified by chromatography on silica gel
  7. washeluting with CH2Cl2/EtOAc (19:1)
  8. customfollowed by recrystallization from CH2Cl2/iPr2O

Sources & evidence

ORD record
ord-568409c3a28f4a30b3427a37157fd415
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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