1,2-Dichloroethane → HCID 86602431, compound

HRID 2252293Notes

Reaction equation

HRID 2252293 reaction equation
[C:1]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][C:4]([O:7][C:8]2[C:9](=[O:27])[N:10]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:11]=[CH:12][C:13]=2[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:3][CH:2]=1.[C:34](N[C@H](C(O)=O)C)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[O:68]1C[CH2:71][CH2:70][CH2:69]1>ClCCl>[C:1]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][C:4]([O:7][C:8]2[C:9](=[O:27])[N:10]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:11]=[CH:12][C:13]=2[N:14]2[CH2:19][CH2:18][N:17]([C:69](=[O:68])[CH:70]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH3:71])[CH2:16][CH2:15]2)=[CH:3][CH:2]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanineHCID 16754447HCID 16754447, compound

Product 1

HCID 86602431HCID 86602431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

160 mg (0.348 mmol) of the compound from Example 12, dissolved in 1 ml of dichloromethane, are added dropwise to a solution of 92 mg (0.487 mmol) of Boc-L-alanine, 93.4 mg (0.487 mmol) of EDC, 65.8 mg (0.487 mmol) of HOBt and 0.1 ml (0.717 mmol) of triethylamine in 2 ml of tetrahydrofuran and 10 ml of dichloromethane while stirring under argon at 0° C. The mixture is stirred at room temperature overnight. The reaction solution is diluted with 100 ml of dichloromethane, washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated. The residue is stirred with ether and filtered off with suction.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. stirringThe residue is stirred with ether
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-bfdf4ee15c1e4e708a07013c62fc5c87
Source dataset
uspto-grants-2008_01
Patent number
US07320977B2

Reaction notes

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