Benzyl chloroformate → HCID 86635438, compound
Reaction equation
[NH2:1][C:2]1[C:3]2[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][C:4]=2[NH:5][N:6]=1.C(N(CC)C(C)C)(C)C.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:30]([O:29][C:27]([NH:1][C:2]1[C:3]2[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7][C:4]=2[NH:5][N:6]=1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To the product from Step A (133 mg) in dichloromethane (3 mL) at 0° C. was added N,N-diisopropylethylamine (0.21 mL) followed by benzyl chloroformate (0.1 mL). The reaction mixture was stirred at 0° C. for 90 min, then diluted with dichloromethane (10 mL) and poured into saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous phase extracted with dichloromethane (3×10 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified on a Biotage Horizon® system (silica gel, 0 to 80% ethyl acetate/hexanes gradient) to give the title compound. LC/MS 359.3 (M+1).
Workup
- customThe layers were separated
- extractionthe aqueous phase extracted with dichloromethane (3×10 mL)
- dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customThe residue was purified on a Biotage Horizon® system (silica gel, 0 to 80% ethyl acetate/hexanes gradient)
Sources & evidence
- ORD record
- ord-1a1d89eef63c47a58b020581e2c05d26
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750034B2
Reaction notes
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