1,2-Dichloroethane → HCID 131725918, compound
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7](O)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(Cl)C[Cl:19].C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:32][C@@H:33]([CH2:45][CH3:46])[CH:34]([C:36]1[O:37][C:38]2[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=2[N:40]=1)[OH:35].CN1CCOCC1>ClCCl>[ClH:19].[O:37]1[C:38]2[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=2[N:40]=[C:36]1[CH:34]([OH:35])[C@@H:33]([NH:32][C:7](=[O:8])[C@@H:2]([NH2:1])[CH2:3][CH:4]([CH3:6])[CH3:5])[CH2:45][CH3:46]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Boc-Leu-OH (350 mg, 1.40 mmol) was combined with EDC (500 mg, 2.6 mmol), HOBt (250 mg, 1.6 mmol), and (2S)-2-amino-1-benzoxazol-2-yl-butan-1-ol hydrochloride (300 mg, 1.24 mmol). Dichloromethane (10 mL) was added and then 4-methylmorpholine (1 mL). The reaction mixture was stirred at ambient temperature for 2 h. After dilution with ethyl acetate (150 mL), the solution was washed with 1N aqueous HCl, water, saturated aqueous NaHCO3 solution and brine, dried with MgSO4 and evaporated under vacuum. The crude product was dissolved in 4N HCl/dioxane solution and stirred for 2 h. Evaporation to dryness gave (S)-2-amino-4-methyl-pentanoic acid(S)-[1-(benzoxazol-2-yl-hydroxy-methyl)-propyl]-amide hydrochloride (450 mg) as brownish oil.
Workup
- washAfter dilution with ethyl acetate (150 mL), the solution was washed with 1N aqueous HCl, water, saturated aqueous NaHCO3 solution and brine
- dry with materialdried with MgSO4
- customevaporated under vacuum
- dissolutionThe crude product was dissolved in 4N HCl/dioxane solution
- stirringstirred for 2 h
- customEvaporation to dryness
Sources & evidence
- ORD record
- ord-4b5abd99997940fe8e71290c867cc98c
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101880B2
Reaction notes
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