Diethyl Ether → HCID 44229901, compound

HRID 1026818Notes

Reaction equation

HRID 1026818 reaction equation
[CH:1]1([NH:4][C:5](=[O:43])[NH:6][C:7]2[CH:41]=[CH:40][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH2:36][CH2:37][O:38][CH3:39])C(=O)OC(C)(C)C)=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:42])[CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.C(OCC)C>ClCCl>[CH:1]1([NH:4][C:5]([NH:6][C:7]2[CH:41]=[CH:40][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[CH:22]=[CH:23][C:24]([CH2:27][NH:28][CH2:36][CH2:37][O:38][CH3:39])=[CH:25][N:26]=5)[S:20][C:13]=34)=[C:9]([F:42])[CH:8]=2)=[O:43])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 58236588HCID 58236588, compound

Product 1

HCID 44229901HCID 44229901, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 338 (0.19 g, 0.31 mmol) in dichloromethane (40 mL) was added TFA (3 mL). The solution was stirred for 6 h, then concentrated. The residue was partitioned between 98:2 dichloromethane/methanol mixture and 1M NaOH(aq), washed with brine, dried over MgSO4, filtered and concentrated. The resulting oil was triturated with diethyl ether and ethyl acetate providing 339 (0.13 g, 82% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 1H: 8.80 (s, 1H); 8.57 (s, 1H); 8.51 (d, J=5.5, 1H); 8.31 (s, 1H); 8.23 (d, J=8.0, 1H); 7.89 (dd, J=8.0, 1.5, 1H); 7.73 (dd, J=13.5, 2.2, 1H); 7.38 (t, J=9.0, 1H); 7.20 (d, J=8.2, 1H); 6.66-6.62 (m, 2H); 3.78 (s, 2H); 3.41 (t, J=5.7, 2H); 3.24 (s, 3H); 2.65 (d, J=5.7, 2H); 2.57-2.51 (m, 1H); 0.66-0.62 (m, 2H); 0.44-0.41 (m, 2H). MS (m/z): 508.3 (M+H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 98:2 dichloromethane/methanol mixture and 1M NaOH(aq)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8dcf430f246d407da5ab38cf13a90c73
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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