1,2-Dichloroethane → HCID 11122634, compound
Reaction equation
[CH3:1][C:2]([CH3:26])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C@H:9]([C:23]([NH2:25])=[O:24])[CH2:8]1)=[O:6])[CH3:3].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:41](N)([CH3:44])([CH3:43])[CH3:42].C(N(CC)CC)C>CN(C=O)C>[C:41]([NH:25][C:23]([C@@H:9]1[CH2:8][N:7]([C:5]([O:4][C:2]([CH3:26])([CH3:1])[CH3:3])=[O:6])[CH2:12][CH2:11][N:10]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=[O:24])([CH3:44])([CH3:43])[CH3:42]Participants
Conditions
- Temperature
- 0 °C
Procedure
To 9.90 g (27.16 mmol) of 4-(1,1-dimethylethoxy-carbonyl)-1-(phenylmethoxycarbonyl)-piperazine-2(S)-carboxamide dissolved in 75 mL of DMF and cooled to 0° C. were added 5.73 g (29.88 mmol) of EDC, 4.03 g (29.88 mmol) of HOBt, 3.14 mL (29.88 mmol) of t-butylamine, and finally 4.16 mL (29.88 mmol) of triethylamine. The reaction mixture was stirred for 18 hours and the reaction volume was concentrated under reduced pressure. The residue was then diluted with 600 mL of EtOAc and washed with 10% HCl (2×75 mL), saturated NaHCO3 (1×75 mL), water (3×75 mL) and brine (1×50 mL), dried over MgSO4 and concentrated to a solid. This solid was triturated with EtOAc: hexane (1:2) and filtered to provide the title compound as a white solid; mp 134°-135° C.
Workup
- concentrationthe reaction volume was concentrated under reduced pressure
- additionThe residue was then diluted with 600 mL of EtOAc
- washwashed with 10% HCl (2×75 mL), saturated NaHCO3 (1×75 mL), water (3×75 mL) and brine (1×50 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated to a solid
- customThis solid was triturated with EtOAc: hexane (1:2)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-0845a48f872f4801ac06c2849ae727bf
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05650412
Reaction notes
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