1,2-Dichloroethane → HCID 66836374, compound
Reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)CCl.C(N(CC)CC)C.[C:31]12([CH2:41]O)[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]3)[CH2:32]1)[CH2:38]2>ClCCl.CN(C1C=CN=CC=1)C>[C:4]([O:3][C:1]([NH:8][C@H:9]([C:17]([O:19][CH2:41][C:31]12[CH2:40][CH:35]3[CH2:34][CH:33]([CH2:39][CH:37]([CH2:36]3)[CH2:38]1)[CH2:32]2)=[O:18])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:2])([CH3:5])([CH3:7])[CH3:6]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 500 mg (1.89 mmol) of N-Boc-L-phenylalanine in 25 ml of dichloromethane were added, at RT, 1192 mg (6.2 mmol) of EDC, 578 μl (4.1 mmol) of triethylamine, 345 mg (2.8 mmol) of DMAP and 345 mg (2.1 mmol) of 1-adamantylmethanol. The reaction mixture was stirred overnight, then diluted with 50 ml of dichloromethane, and was successively washed with 10% aqueous citric acid solution, water and saturated sodium chloride solution. The organic phase was dried over magnesium sulphate, then concentrated, and the residue was purified by preparative HPLC. 769 mg (90% of theory) of the title compound were obtained.
Workup
- washwas successively washed with 10% aqueous citric acid solution, water and saturated sodium chloride solution
- dry with materialThe organic phase was dried over magnesium sulphate
- concentrationconcentrated
- customthe residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-0065df7051934ca1a6efd9ba146748b2
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08992932B2
Reaction notes
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