Potassium Carbonate → HCID 68691453, compound

HRID 2238438Notes

Reaction equation

HRID 2238438 reaction equation
[CH2:1]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[S:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[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(=O)N([Br:44])C(=O)C1.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:44][C:19]1[C:20]2[C:15](=[CH:14][CH:13]=[C:12]([S:9]([N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)(=[O:11])=[O:10])[CH:21]=2)[CH:16]=[CH:17][C:18]=1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 68692696HCID 68692696, compound

Product 1

HCID 68691453HCID 68691453, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 211 (1.15 g, 2.29 mmol), NBS (450 mg, 2.52 mmol), and K2CO3 (380 mg, 2.75 mmol) in MeCN (25 mL) was stirred at 40° C. under nitrogen for 30 min. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and H2O. The EtOAc layer was washed with H2O, brine, then dried and evaporated. The residue was recrystallised from EtOAc/Et2O/petroleum ether to give tert-butyl 1-bromo-7-[(dibenzylamino)sulfonyl]-2-naphthylcarbamate (212) as colorless crystals: mp 150-151° C.; 1H NMR (CDCl3) δ 8.69 (d, J=1.6 Hz, 1H), 8.57 (d, J=9.1 Hz, 1H), 7.89 (d, J=8.6 Hz, 1H), 7.85 (d, J=9.1 Hz, 1H), 7.74 (dd, J=8.6, 1.8 Hz, 1H), 7.38 (s, 1H), 7.22-7.15 (m, 6H), 7.12-7.05 (m, 4H), 4.40 (s, 4H), 1.58 (s, 9H); 13C NMR δ 152.4, 139.6, 136.5, 135.5, 132.0, 131.5, 129.7, 128.6, 128.5, 128.1, 127.7, 126.8, 122.1, 121.8, 110.4, 81.8, 50.6, 28.3. Anal. (C29H29BrN2O4S) C, H, N.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe EtOAc layer was washed with H2O, brine
  4. customdried
  5. customevaporated
  6. customThe residue was recrystallised from EtOAc/Et2O/petroleum ether

Sources & evidence

ORD record
ord-302a65f1bed1452991ab5f8ea48c6a1f
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

Loading…